O-methyl hydrazinecarbothioate → 5-[2-(4-acetamidophenyl)ethanyl]-5,6-dihydro-1,3,4-thiadiazin-2(3H)one

HRID 893071

Reaction equation

HRID 893071 reaction equation
Cl[CH2:2][C:3](=O)[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1.C[O:18][C:19]([NH:21][NH2:22])=[S:20]>C1(C)C=CC=CC=1>[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH:3]2[CH2:2][S:20][C:19](=[O:18])[NH:21][NH:22]2)=[CH:7][CH:8]=1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 10171237O-methyl hydrazinecarbothioateHCID 540553571-Chloro-4-(4-acetamidophenyl)-2-oxo-3-butene

Product 1

HCID 198927595-[2-(4-acetamidophenyl)ethanyl]-5,6-dihydro-1,3,4-thiadiazin-2(3H)one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture containing 4.0 g of 1-chloro-4-(4-acetamidophenyl)-2-oxo-3-butene (J. Org. Chem., 28, 2446, 1963) and 2.3 g of hydrazinecarbothioic acid O-methylester in 150 ml of toluene was refluxed for 3 h. The crystals were filtered and washed with toluene. Yield 3.0 g (65%), mp. 235°-240° C.

Workup

  1. temperaturewas refluxed for 3 h
  2. filtrationThe crystals were filtered
  3. washwashed with toluene

Sources & evidence

ORD record
ord-65cfd78dde2b431692ae86f4e96337a8
Source dataset
uspto-grants-1992_06
Patent number
US05122524

Linked notes

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