2-Pyrimidinamine, 4-chloro-6-methoxy- → Chlorimuron-ethyl

HRID 236523

Reaction equation

HRID 236523 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([O:9][CH3:10])[N:3]=1.[N:11]([S:14]([C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:16])=[O:15])=[C:12]=[O:13]>C(Cl)Cl>[CH2:22]([O:21][C:19](=[O:20])[C:18]1[CH:24]=[CH:25][CH:26]=[CH:27][C:17]=1[S:14]([NH:11][C:12]([NH:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([O:9][CH3:10])[N:3]=1)=[O:13])(=[O:15])=[O:16])[CH3:23]

Participants

4

Reactant 2

HCID 798112-Pyrimidinamine, 4-chloro-6-methoxy-HCID 13386652Benzoic acid, 2-(isocyanatosulfonyl)-, ethyl ester

Product 1

HCID 56160Chlorimuron-ethyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1.0 g of 2-amino-4-chloro-6-methoxypyrimidine suspended in 25 ml of dry CH2Cl2 was added 1.53 g of ethyl 2-(isocyanatosulfonyl)benzoate (prepared by procedures taught in U.S. Pat. No. 4,305,884). The reaction mixture was stirred at ambient temperature for three days. The solvent was stripped and the product was recrystallized from butyl chloride to give a white solid with m.p. 198°-201°.

Workup

  1. customprepared by procedures
  2. customthe product was recrystallized from butyl chloride
  3. customto give a white solid with m.p. 198°-201°

Sources & evidence

ORD record
ord-eb4dcd838c1f489f9e4d50c14c536e5d
Source dataset
uspto-grants-1987_02
Patent number
US04645530

Linked notes

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