2-Amino-4,6-dimethyl pyrimidine → Sulfometuron-methyl

HRID 464121Notes

Reaction equation

HRID 464121 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[O-:10][C:11]#[N:12].[Na+].[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25])([O:16][CH3:17])=[O:15]>C(#N)C.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:11]([NH:12][S:24]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:14]([O:16][CH3:17])=[O:15])(=[O:26])=[O:25])=[O:10])[N:3]=1

Participants

6

Reactant 3

HCID 130212-Amino-4,6-dimethyl pyrimidineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 517096Sodium Cyanate

Product 1

HCID 52997Sulfometuron-methyl

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A slurry of 7.0 grams (0.057 moles) of 4,6-dimethyl-2-pyrimidinamine, 6.0 grams (0.092 moles) sodium cyanate, and 13.5 grams (0.057 moles) 2-carbomethoxybenzenesulfonyl chloride in 60 ml acetonitrile was stirred 1 hour at reflux (81°). The reaction was diluted with 60 ml water, allowed to cool to room temperature and filtered. The solid was washed with 20 ml water and dried. There was obtained 16.0 grams (77.0% of theory) of the title compound. The product was 98% pure as assayed by high pressure liquid chromatography. The m.p. and IR spectrum of the title compound were identical to those of an authentic sample prepared as described in U.S. Pat. No. 4,394,506.

Workup

  1. temperatureat reflux (81°)
  2. filtrationfiltered
  3. washThe solid was washed with 20 ml water
  4. customdried

Sources & evidence

ORD record
ord-4a31736aa644424591cac2c226fff716
Source dataset
uspto-grants-1985_10
Patent number
US04546179

Reaction notes

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