O-Ethyl hydrazinecarbothioate → HCID 59569025, compound

HRID 1517194Notes

Reaction equation

HRID 1517194 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9](Br)[CH3:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[NH:16]([C:18](=[S:22])[O:19]CC)[NH2:17]>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:10])[S:22][C:18](=[O:19])[NH:16][N:17]=2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 12567113O-Ethyl hydrazinecarbothioateHCID 595690141-(4-Amino-3-nitrophenyl)-2-bromopropan-1-one

Product 1

HCID 59569025HCID 59569025, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

36.5 g (134 mM) of 1-(4-amino-3-nitrophenyl)-2-bromopropan-1-one and 24.3 g (202.5 mM) of O-ethyl hydrazinecarbothioate dissolved in 190 ml of acetonitrile are refluxed for 4 hours with stirring. The reaction mixture is cooled and maintained at 0° C. for 16 hours. The crystalline solid is filtered off and washed with cold acetonitrile to give, after drying, 10.4 g of 5-(4-amino-3-nitrophenyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in the form of a solid.

Workup

  1. temperatureare refluxed for 4 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe crystalline solid is filtered off
  4. washwashed with cold acetonitrile
  5. customto give
  6. customafter drying

Sources & evidence

ORD record
ord-8ff24e79618c4be0b662b3b99b90d54d
Source dataset
uspto-grants-2012_07
Patent number
US08232272B2

Reaction notes

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