Bromine → 5,7-dimethoxy-2-[(2-methoxycarbonylbenzyl)sulfonyl]imino-2H-[1,2,4]-thiadiazolo[2,3-a]pyrimidine

HRID 330454Notes

Reaction equation

HRID 330454 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:28]=[CH:27][CH:26]=[CH:25][C:6]=1[CH2:7][S:8]([NH:11][C:12]([NH:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[N:16]=1)=[S:13])(=[O:10])=[O:9])=[O:4].BrBr>N1C=CC=CC=1>[CH3:24][O:23][C:17]1[CH:18]=[C:19]([O:21][CH3:22])[N:20]2[S:13][C:12](=[N:11][S:8]([CH2:7][C:6]3[CH:25]=[CH:26][CH:27]=[CH:28][C:5]=3[C:3]([O:2][CH3:1])=[O:4])(=[O:10])=[O:9])[N:14]=[C:15]2[N:16]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 14275714N-(2-Methoxycarbonylbenzyl)sulfonyl-N'-(4,6-dimethoxy-2-pyrimidinyl) thiourea

Product 1

HCID 536931185,7-dimethoxy-2-[(2-methoxycarbonylbenzyl)sulfonyl]imino-2H-[1,2,4]-thiadiazolo[2,3-a]pyrimidineYield 78.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(2-Methoxycarbonylbenzyl)sulfonyl-N'-(4,6-dimethoxy-2-pyrimidinyl) thiourea (1.0 g) is dissolved in 15 ml of pyridine and cooled to -10°~-5° C., to which 0.4 g of bromine is dropwise added. After stirring for 1.5 hours at the same temperature, the reaction mixture is poured into 100 ml of ice water and the white crystals are collected by filtration. The product is washed with water, dried and washed with hot acetonitrile to give 0.78 g of the title compound as white powdery crystals. mp 153°~154° C.

Workup

  1. additionis dropwise added
  2. filtrationthe white crystals are collected by filtration
  3. washThe product is washed with water
  4. customdried
  5. washwashed with hot acetonitrile

Sources & evidence

ORD record
ord-1a07ee0a836844969513b249e1efca91
Source dataset
uspto-grants-1990_01
Patent number
US04897105

Reaction notes

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