Triphosgene → 4-Methoxycarbonylphenyl-pentyl-carbamoyl chloride
Reaction equation
[CH2:1]([NH:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[Cl:17][C:18](Cl)([O:20]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[CH3:14][O:13][C:11]([C:10]1[CH:9]=[CH:8][C:7]([N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:18]([Cl:17])=[O:20])=[CH:16][CH:15]=1)=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of methyl 4-pentylaminobenzoate (43) (200 mg, 0.91 mmole) in 5 mL of THF was treated with 95 mg of triphosgene (0.35 eq.), stirred at reflux for three hours, then poured onto 50 mL ice-water and extracted with three portions of 50 mL of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give 250 mg of 4-methoxycarbonylphenyl-pentyl-carbamoyl chloride (45) which was used without purification.