Methyl chloroformate → 2-(Methoxycarbonylaminomethyl)aniline

HRID 863216Notes

Reaction equation

HRID 863216 reaction equation
[NH2:1][CH2:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].Cl[C:11]([O:13][CH3:14])=[O:12]>C(Cl)Cl.C(N(C(C)C)CC)(C)C>[CH3:14][O:13][C:11]([NH:1][CH2:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])=[O:12]

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 1780962-(Aminomethyl)aniline

Product 1

HCID 121757882-(Methoxycarbonylaminomethyl)aniline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

The amine component employed is obtained starting from 2.0 g of 2-(aminomethyl)aniline, dissolved in 30 ml of methylene chloride, by reaction with 1.3 ml of methyl chloroformate in the presence of 3.1 ml of diisopropylethylamine at 5° C. After purification over 80 g of silica gel (mobile phase A), 2-(methoxycarbonylaminomethyl)aniline is obtained: Rf (A)=0.23; Rf (Z)=0.31.

Workup

  1. customAfter purification over 80 g of silica gel (mobile phase A)

Sources & evidence

ORD record
ord-d706756d84c845f7ad0a6606c39d53d8
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

Loading…