Hydrazine hydrate (1:1) → HCID 131729068, compound

HRID 1014896Notes

Reaction equation

HRID 1014896 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][O:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:14]=2[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:6]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:5]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([O-])=O.O.NN>CO>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([S:12][O:11][S:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[C:5]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:6]=2[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:14]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:15]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 131729069HCID 131729069, compound

Product 1

HCID 131729068HCID 131729068, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
62.5 °C

Procedure

To 500 parts of methanol, 115 parts of para-nitrophenyl-o-carbethoxyphenylthio ether, 10 parts of activated carbon and 1 part of ferric chloride hexahydrate were added, and the mixture was stirred at a liquid temperature of 60 to 65° C. for 20 minutes. To this reaction liquid, a mixture of 68 parts of 80% hydrazine monohydrate and 100 parts of methanol were added dropwise over 1 hour while maintaining the liquid temperature at 65° C. or less, and reaction was further carried out at the same temperature for 3 hours. The mother liquid obtained by filtration of the reaction liquid was concentrated and the precipitated solid was washed with water and dried to obtain 95.4 parts of para-aminophenyl-o-carbethoxyphenylthio ether which is the title compound.

Workup

  1. customTo this reaction liquid
  2. additionwere added dropwise over 1 hour
  3. temperaturewhile maintaining the liquid temperature at 65° C. or less
  4. customreaction
  5. waitwas further carried out at the same temperature for 3 hours
  6. customThe mother liquid obtained by filtration of the reaction liquid
  7. concentrationwas concentrated
  8. washthe precipitated solid was washed with water
  9. customdried

Sources & evidence

ORD record
ord-14169b1ac1ee423fa410473cac5fac91
Source dataset
uspto-grants-2011_07
Patent number
US07985287B2

Reaction notes

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