Chloroacetyl chloride → S-Metolachlor

HRID 1872413Notes

Reaction equation

HRID 1872413 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([NH:6][C:7]1[C:12]([CH2:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:15])[CH3:5].[Cl:16][CH2:17][C:18](Cl)=[O:19]>>[Cl:16][CH2:17][C:18]([N:6]([C:7]1[C:12]([CH2:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:15])[C@@H:4]([CH3:5])[CH2:3][O:2][CH3:1])=[O:19]

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 10130489Benzenamine, 2-ethyl-N-[(1S)-2-methoxy-1-methylethyl]-6-methyl-

Product 1

HCID 11140605S-Metolachlor

Procedure

(S)-N-(1-Methoxyprop-2-yl)-2-methyl-6-ethylphenylamine is acylated with chloroacetyl chloride in a manner known per se to yield the known (S)-N-chloroacetyl-N-(1-methoxyprop-2-yl)-2-methyl-6-ethylphenylamine (also known as S-metolachor).

Sources & evidence

ORD record
ord-26be245fca9d4097a1fa3808a199d2f1
Source dataset
uspto-grants-2000_08
Patent number
US06107521

Reaction notes

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