cyclohexyl carbonochloridate

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:

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: To a solution of N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-1-heptanamine (0.87 g, 0.002 mol) and sodium bicarbonate (5%, 1 mL) in toluene (10 mL) at 0° was added, dropwise, a solution of cyclohexylchloroformate (0.32 g, 0.002 mol) in toluene (5 mL). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The solvent was removed under vacuum. The residue (1.0 g) was chromatographed with 7:3 hexane-ethyl acetate to give the title compound (0.61 g, 0.0011 mol) as a yellow oil. 1H NMR (CDCl3) δ11.1(bs,1H), 7.7-7.2(m,10H), 4.6(bs,1H), 3.3(t,2H,J=5.1Hz), 3.2(t,2H,J=7.5Hz), 3.0(t,2H,J=5.2Hz), 1.9-1.2(m,26H), 0.9-0.8(m,3H). The solvent was removed under vacuum The residue (1.0 g) was chromatographed with 7:3 hexane-ethyl acetate

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

Procedure: From 24.8 g (0.20 mole) of trimethylphosphite and 32.1 g (0.20 mole) of cyclohexylchloroformate, (Y. Iwakura and A. Nabeya, J. Org. Chem. 25 (1960) 1118; M. E. Fourneau et al. Chem. Abstr. 16 (1922) 240; J. H. Saunders et al. J. Am. Chem. Soc. 73 (1951) 3797). (100° C., 2 hours). Yield 30 g (54%). Bp1.4-1.8 148°-151° C. nD21 1.4543. (100° C., 2 hours) Bp1.4-1.8 148°-151° C.

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

Procedure: From 24.8 g (0.20 mole) of trimethylphosphite and 32.1 g (0.20 mole) of cyclohexylchloroformate, (Y. Iwakura and A. Nabeya, J. Org. Chem. 25 (1960) 1118; M. E. Fourneau et al. Chem. Abstr. 16 (1922) 240; J. H. Saunders et al. J. Am. Chem. Soc. 73 (1951) 3797). (100° C., 2 hours). Yield 30 g (54%). Bp1.4-1.8 148°-151° C. nD21 1.4543. (100° C., 2 hours) Bp1.4-1.8 148°-151° C.

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

Procedure: To a solution of N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-1-heptanamine (0.87 g, 0.002 mol) and sodium bicarbonate (5%, 1 mL) in toluene (10 mL) at 0° was added, dropwise, a solution of cyclohexylchloroformate (0.32 g, 0.002 mol) in toluene (5 mL). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The solvent was removed under vacuum. The residue (1.0 g) was chromatographed with 7:3 hexane-ethyl acetate to give the title compound (0.61 g, 0.0011 mol) as a yellow oil. 1H NMR (CDCl3) δ 11.1(bs,1H), 7.7-7.2(m,10H), 4.6(bs,1H), 3.3(t,2H,J=5.1 Hz), 3.2(t,2H,J=7.5 Hz), 3.0(t,2H,J=5.2 Hz), 1.9-1.2(m,26H), 0.9-0.8(m,3H). The solvent was removed under vacuum The residue (1.0 g) was chromatographed with 7:3 hexane-ethyl acetate

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

Procedure: From 24.8 g (0.20 mole) of trimethylphosphite and 32.1 g (0.20 mole) of cyclohexylchloroformate. (Y. Iwakura and A. Nabeya, J. Org. Chem. 25 (1960) 1118; M. E. Fourneau et al. Chem. Abstr. 16 (1922) 240; J. H. Saunders et al. J. Am. Chem. Soc. 73 (1951) 3797). (100° C., 2 hours). Yield 30 g (64%). Bp1.4-1.8 148°-151° C. nD21 1.4543. (100° C., 2 hours) Bp1.4-1.8 148°-151° C.

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

Procedure: From 24.8 g (0.20 mole) of trimethylphosphite and 32.1 g (0.20 mole) of cyclohexylchloroformate. (Y. Iwakura and A. Nabeya, J. Org. Chem. 25 (1960) 1118; M. E. Fourneau et al. Chem. Abstr. 16 (1922) 240; J. H. Saunders et al. J. Am. Chem. Soc. 73 (1951) 3797). (100° C., 2 hours). Yield 30 g (64%). Bp1.4-1.8 148°-151° C. nD21 1.4543. (100° C., 2 hours) Bp1.4-1.8 148°-151° C.