Hydrazine hydrate (1:1) → HCID 10059583, compound

HRID 1742093Notes

Reaction equation

HRID 1742093 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][NH:9][C:10](=S)[S:11]C)=[CH:6][CH:5]=1)([O-:3])=[O:2].O.[NH2:17][NH2:18]>C(O)C>[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][NH:9][C:10](=[S:11])[NH:17][NH2:18])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10014629HCID 10014629, compound

Product 1

HCID 10059583HCID 10059583, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 187 g (772 mmole) of methyl N-(4-nitrobenzyl)dithiocarbamate and 450 ml of hydrazine hydrate in 1400 ml of absolute ethanol was stirred mechanically and heated to reflux. Precipitation began by the time the internal temperature reached about 40° C. After 2 hours at reflux, the mixture was cooled and allowed to stand at room temperature. The solid was collected on a filter, washed with ethanol, and dried to give 105 g (60%) of light yellow crystals, mp 196°-198° C. satisfactory purity by TLC in 95:5:0.5 CH2Cl2 --MeOH-concd NH4OH; mass spectrum (FAB) m/e 227 (M+1)+.

Workup

  1. temperatureheated to reflux
  2. customPrecipitation
  3. customreached about 40° C
  4. temperatureAfter 2 hours at reflux
  5. temperaturethe mixture was cooled
  6. customto stand at room temperature
  7. customThe solid was collected on a filter
  8. washwashed with ethanol
  9. customdried
  10. customto give 105 g (60%) of light yellow crystals, mp 196°-198° C. satisfactory purity by TLC in 95:5:0.5 CH2Cl2

Sources & evidence

ORD record
ord-79b8742cd0e14d4081532b2f204b069c
Source dataset
uspto-grants-1994_08
Patent number
US05336778

Reaction notes

Loading…