9H-xanthene-9-carbonyl chloride

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, white solid, m.p. 186° C. and MS: m/e=307 (M+) was prepared in accordance with the general method of example 44a from 5-methyl-[1,2,4]oxadiazol-3-ylamine and 9H-xanthene-carboxylic acid chloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, white solid, m.p. 275° C. and MS: m/e=333 (M+) was prepared in accordance with the general method of example 44a from 3-cyclopropyl-[1,2,4]oxadiazol-5-ylamine and 9H-xanthene-carboxylic acid chloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, white solid, m.p. 208° C. and MS: m/e=307 (M+) was prepared in accordance with the general method of example 44a from 3-methyl-[1,2,4]oxadiazol-5-ylamine and 9H-xanthene-carboxylic acid chloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, white solid, m.p. 203-205° C. and MS: m/e=334.1 (M+) was prepared in accordance with the general method of example 44a from 5-propyl-oxazol-2-ylamine [Ber. 95,2419(1962)] and 9-xanthene-carboxylic acid chloride. 66b) The 5-propyl-oxazol-2-ylamine used in the above reaction was obtained as follows: 21.8 g (0.132 mol) of 2-bromobutyraldehyde [Chem.Ber., 70,1898(1937)] was dissolved in 67.5 ml of a 4:3 mixture of DMF and water. Urea, 8.77 g (0.145 mol) was added with stirring. The clear colorless solution was stirred for 16 h at 105° C. The resulting light yellow solution is cooled to 0° C. and 10 ml of 45% Sodium hydroxide solution was added. The solution turns dark yellow (pH 12). 100 ml of brine is added and the solution is extracted five times with 100 ml of a 9:1 mixture of methylene chloride and methanol. The combined organic phases were concentrated to yield 15.62 g of a reddish brown oil which was purified by flash chromatography on silica gel with a 9:1 mixture of methylene chloride and methanol as eluent. One obtains 6.2 g (0.049 mol, 37%) of 5-5-propyl-oxazol-2-ylamine as a yellow oil which was directly used without further purification, MS: m/e=126.1 (M+).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, white solid, m.p. 217-220° C. and MS: m/e=306.1 (M+) was prepared in accordance with the general method of example 44a from 5-methyl-oxazol-2-ylamine [Ber. 95, 2419(1962)] and 9-xanthene-carboxylic acid chloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, white solid, m.p. 212-213° C. and MS: m/e=320.1 (M+) was prepared in accordance with the general method of example 44a from 5-ethyl-oxazol-2-ylamine [Ber. 95, 2419(1962)] and 9-xanthene-carboxylic acid chloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, white solid, m.p. 261-263° C. and MS: m/e=307.1 (M+) was prepared in accordance with the general method of example 44a from 5-methyl[1,3,4]oxadiazol-2-ylamine and 9-xanthene-carboxylic acid chloride. The 5-methyl[1,3,4]oxadiazol-2-ylamine, white solid, MS: m/e=99 (M+) used in the above reaction was prepared in accordance with the general method of example 48b from acetic acid hydrazide and cyanogen bromide.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, white solid, m.p. 239-240° C. and MS: m/e=293 (M+) was prepared in accordance with the general method of example 44a from [1,3,4]oxadiazol-2-ylamine and 9-xanthene-carboxylic acid chloride. The [1,3,4]oxadiazol-2-ylamine, white solid, MS: m/e=85 (M+) used in the above reaction was prepared in accordance with the general method of example 44b from formic acid hydrazide and cyanogen bromide.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, white solid, m.p.=232-235° C., MS: m/e=292 (M+) was prepared in accordance with the general method of example 31 from 9H-xanthene-9-carbonyl chloride and 2-amino-oxazole.