Phosgene → HCID 23324009, compound

HRID 1381282Notes

Reaction equation

HRID 1381282 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([NH:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[C:15](Cl)([Cl:17])=[O:16]>C(Cl)Cl>[Cl:17][C:15]([N:7]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:6]1[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:16]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 24326633-(4-Methoxy-phenylamino)-propionic acid

Product 1

HCID 23324009HCID 23324009, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By working in a manner similar to that described in Example 6, but starting from 3-(4-methoxyanilino)propionic acid (2.88 g; 14.7 mmol), methylene chloride (20 cc) and phosgene (4.3 g; 43.5 mmol), almost pure N-chloroformyl-3-(4-methoxyanilino)propionic acid (3.77 g) is obtained in the form of a white powder which melts at 90° C. After recrystallisation in a hexane/ethyl acetate mixture (50:50 by volume), the product melts at 93° C. The structure of the product obtained is confirmed by the infrared spectrum, mass spectrum and proton nuclear magnetic resonance spectrum.

Sources & evidence

ORD record
ord-e5fc9f4596bc4367963f230b502c91eb
Source dataset
uspto-grants-1986_04
Patent number
US04585867

Reaction notes

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