4-Chloroaniline → Alanine, N-((p-chlorophenyl)carbamoyl)-2-methyl-, methyl ester

HRID 224943

Reaction equation

HRID 224943 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C:4]([N:7]=[C:8]=[O:9])([CH3:6])[CH3:5].[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>O1CCCC1>[CH3:1][O:2][C:3](=[O:10])[C:4]([CH3:6])([CH3:5])[NH:7][C:8](=[O:9])[NH:16][C:15]1[CH:17]=[CH:18][C:12]([Cl:11])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 2769374Methyl 2-isocyanato-2-methylpropanoate

Product 1

HCID 1252008Alanine, N-((p-chlorophenyl)carbamoyl)-2-methyl-, methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 17.0 g (119 mmol) of 2-isocyanato-2-methylpropionic acid methyl ester in 150 ml of absolute tetrahydrofuran was added, over a 15 minute period to 15.1 g (119 mmol) of p-chloroaniline in 300 ml of absolute tetrahydrofuran. After refluxing the mixture for three days, the solution was evaporated to dryness. The product, after two recrystallizations from methylene chloride, was dried for 6 hours at 40° C., under greatly reduced pressure, to yield N-[(4-chlorophenyl)-carbamoyl]-2-methylalanine methyl ester, m.p. 147°-148° C.

Workup

  1. temperatureAfter refluxing the mixture for three days
  2. customthe solution was evaporated to dryness
  3. customThe product, after two recrystallizations from methylene chloride
  4. customwas dried for 6 hours at 40° C., under greatly reduced pressure

Sources & evidence

ORD record
ord-4cf93b30dd0545c882f2b28327abb08d
Source dataset
uspto-grants-1980_11
Patent number
US04234736

Linked notes

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