O-Xylene → Acetic acid 2-(aminothioxomethyl)-1-(4-methoxyphenyl)hydrazide

HRID 1389498Notes

Reaction equation

HRID 1389498 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][C:11](=[S:13])[NH2:12])=[CH:5][CH:4]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15].CC1C=CC=CC=1C.O(C(C)C)C(C)C>O>[NH2:12][C:11](=[S:13])[NH:10][N:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:14](=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 7914Diisopropyl EtherHCID 7918Acetic AnhydrideHCID 28261724-Methoxyphenylthiosemicarbazide

Product 1

HCID 54330889Acetic acid 2-(aminothioxomethyl)-1-(4-methoxyphenyl)hydrazideYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 17.5 parts of 2-(4-methoxyphenyl)hydrazinecarbothioamide, 10 parts of acetic acid anhydride and 90 parts of dimethylbenzene is stirred and refluxed for one hour. The reaction mixture is allowed to cool to room temperature and 2,2'-oxybispropane and water are added. The precipitated product is filtered off and dried, yielding 14.5 parts (89%) of acetic acid 2-(aminothioxomethyl)-1-(4-methoxyphenyl)hydrazide.

Workup

  1. temperaturerefluxed for one hour
  2. filtrationThe precipitated product is filtered off
  3. customdried

Sources & evidence

ORD record
ord-b76fee012ad3406f93dad1757315abd7
Source dataset
uspto-grants-1981_01
Patent number
US04244964

Reaction notes

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