Chloroacetyl chloride → DL-Alanine, N-(chloroacetyl)-N-(2,6-dimethylphenyl)-, methyl ester

HRID 258726

Reaction equation

HRID 258726 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:14])[CH3:5].C(=O)([O-])[O-].[Na+].[Na+].[Cl:22][CH2:23][C:24](Cl)=[O:25]>C1C=CC=CC=1>[CH3:1][O:2][C:3]([CH:4]([N:6]([C:24](=[O:25])[CH2:23][Cl:22])[C:7]1[C:8]([CH3:14])=[CH:9][CH:10]=[CH:11][C:12]=1[CH3:13])[CH3:5])=[O:15]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 94555Methyl N-(2,6-dimethylphenyl)-DL-alaninate

Product 1

HCID 6452743DL-Alanine, N-(chloroacetyl)-N-(2,6-dimethylphenyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

990.3 g (= 4.76 g-moles) of α-(2,6-dimethylanilino)-propionic acid methyl ester is mixed with 605 g (= 5.7 g-moles) of sodium carbonate in 2.5 liters of benzene (absolute). An amount of 455 ml (= 5.7 g-moles) of monochloroacetyl chloride is then added dropwise and sufficiently slowly to ensure that a temperature of 30°-35° in the reaction mixture is not exceeded. After stirring has been maintained overnight at room temperature, the mixture is filtered off, and the filtrate concentrated in a rotary evaporator at ca. 50°. The resulting residue is recrystallised from ligroin (boiling range 65°-90° ). The yield obtained is 1132 g (= 83.8% of theory) of final product, M.P. 92°-94° (compound No. 3).

Workup

  1. customto ensure that a temperature of 30°-35° in the reaction mixture
  2. filtrationthe mixture is filtered off
  3. concentrationthe filtrate concentrated in a rotary evaporator at ca. 50°
  4. customThe resulting residue is recrystallised from ligroin (boiling range 65°-90° )
  5. customThe yield obtained

Sources & evidence

ORD record
ord-70276b4e689f49109141655fea5c0385
Source dataset
uspto-grants-1977_07
Patent number
US04034108

Linked notes

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