2,6-Dimethylaniline → Methyl N-(2,6-dimethylphenyl)-DL-alaninate

HRID 1684264

Reaction equation

[CH3:1][C:2]1[C:7]([N:8](C(COC)=O)[CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH3:10])=[C:6]([CH3:20])[CH:5]=[CH:4][CH:3]=1.CC1C=CC=C(C)C=1N.BrC(C)C([O-])=O.C(=O)([O-])O.[Na+]>>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH3:20])[C:7]=1[NH:8][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH3:10]

Participants

Reactant 4

HCID 68962,6-Dimethylaniline

HCID 42586Metalaxyl

HCID 516892Sodium Bicarbonate

HCID 14535398Alpha-bromopropionate

Product 1

HCID 94555Methyl N-(2,6-dimethylphenyl)-DL-alaninate

Procedure

The preparation of metalaxyl is published in the CH-PS 607,888, according to which 2,6-dimethylaniline is first reacted with methyl DL-α-bromopropionate in the presence of sodium hydrogen carbonate as acid binding agent, then methyl N-(2,6-dimethylphenyl)-DL-alaninate thus obtained is acylated with methoxyacetyl chloride to give metalaxyl.

Sources & evidence

ORD record: ord-477b7476c77943e99d6ea4ee8b9d3031
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639905

Linked notes

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