Bromine → 2-(2-chlorophenylsulfonyl)imino-5-methoxy-7-methyl-2H-[1,2,4]-thiadiazolo [2,3-a]pyrimidine

HRID 330453Notes

Reaction equation

HRID 330453 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]([NH:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([CH3:23])[N:16]=1)=[S:13])(=[O:10])=[O:9].BrBr>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]=[C:12]1[S:13][N:16]2[C:17]([CH3:23])=[CH:18][C:19]([O:21][CH3:22])=[N:20][C:15]2=[N:14]1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 24408BromineHCID 14275697N-(2-chlorophenylsulfonyl)-N'-(4-methoxy-6-methyl-2-pyrimidinyl) thiourea

Product 1

HCID 543714952-(2-chlorophenylsulfonyl)imino-5-methoxy-7-methyl-2H-[1,2,4]-thiadiazolo [2,3-a]pyrimidineYield 70.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2.0 g of N-(2-chlorophenylsulfonyl)-N'-(4-methoxy-6-methyl-2-pyrimidinyl) thiourea in 30 ml of pyridine is cooled to -6° C.~-8° C., to which 0.9 g of bromine is dropwise added. After stirring for 1.5 hours, at the same temperature, the reaction mixture is poured into 150 ml of ice water and the precipitate is collected by filtration. It is then washed with water, dried, and recrystallized from acetonitrile to give 1.4 g of title compound as white needles. mp 191°~192° C. (decomp.)

Workup

  1. additionis dropwise added
  2. filtrationthe precipitate is collected by filtration
  3. washIt is then washed with water
  4. customdried
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-069b4fd103f9467fb12d03e9356b3f9b
Source dataset
uspto-grants-1990_01
Patent number
US04897105

Reaction notes

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