O-Ethyl hydrazinecarbothioate → HCID 70383297, compound

HRID 986388Notes

Reaction equation

HRID 986388 reaction equation
Br.[Br:2][CH2:3][C:4]([C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[N:14][C:9]2=[N:8][C:7]=1[CH3:15])=O.[C:16]([O:20]CC)(=[S:19])[NH:17][NH2:18]>C(#N)C>[BrH:2].[CH3:15][C:7]1[N:8]=[C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]2[C:6]=1[C:4]1[CH2:3][S:19][C:16](=[O:20])[NH:17][N:18]=1

Participants

4

Reactant 2

HCID 12567113O-Ethyl hydrazinecarbothioateHCID 201574453-Bromoacetyl-2-methylimidazo[1,2-a]pyrimidine hydrobromide

Product 1

HCID 70383297HCID 70383297, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5.4 g of 3-bromoacetyl-2-methylimidazo[1,2-a]pyrimidine hydrobromide, 3 g of ethyl thiocarbazate and 100 ml of acetonitrile is stirred under reflux for 4 hours. After cooling, crystals are collected by filtration and recrystallized from methanol twice to give 2 g of 5-(2-methylimidazo[1,2-a]pyrimidin-3-yl)-3,6-dihydro-1,3,4-thiadiazin-2 -one hydrobromide as pale yellow crystals, melting at 285°-288° C. with decomposition.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureAfter cooling
  3. filtrationcrystals are collected by filtration
  4. customrecrystallized from methanol twice

Sources & evidence

ORD record
ord-f7edbaebcd174f399fe5e02574fb8ece
Source dataset
uspto-grants-1987_12
Patent number
US04713381

Reaction notes

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