1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(2-Sulfamoylphenylmethylthio)pyrimidine

HRID 746126Notes

Reaction equation

HRID 746126 reaction equation
N12CCCN=C1CCCCC2.[SH:12][C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1.Cl[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27]([NH2:30])(=[O:29])=[O:28]>C(#N)C.O>[S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][S:12][C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1)(=[O:28])(=[O:29])[NH2:30]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 133646272-(Chloromethyl)benzenesulfonamideHCID 178418793HCID 178418793, compound

Product 1

HCID 200417502-(2-Sulfamoylphenylmethylthio)pyrimidineYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

With cooling, 7.9 g of 97% 1,8-diazabicyclo[5.4.0]undec-7-ene are added to a suspension of 5.7 g of 98% 2-mercaptopyrimidine in 50 ml of acetonitrile. To the yellowish solution so obtained are added 10.3 g of 2-chloromethylbenzenesulfonamide. The reaction solution is stirred for 70 hours at 20°-22° C. and then diluted with 1 liter of water. The precipitate is isolated by filtration and dried, affording 12.0 g (85% of theory) of 2-(2-sulfamoylphenylmethylthio)pyrimidine of m.p. 128°-130° C.

Workup

  1. temperatureWith cooling
  2. customTo the yellowish solution so obtained
  3. customThe precipitate is isolated by filtration
  4. customdried

Sources & evidence

ORD record
ord-11ebf5edaa1d4b7fab2431b5db45a547
Source dataset
uspto-grants-1986_07
Patent number
US04602936

Reaction notes

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