Hydrazine hydrate (1:1) → HCID 70019360, compound

HRID 1280395Notes

Reaction equation

HRID 1280395 reaction equation
CS[C:3]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)=[CH:4][N+:5]([O-:7])=[O:6].O.[NH2:21][NH2:22]>C(O)C>[NH:21]([C:3]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)=[CH:4][N+:5]([O-:7])=[O:6])[NH2:22]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 4322904HCID 4322904, compound

Product 1

HCID 70019360HCID 70019360, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.00 g of 1,1-bis(methylthio)-2-nitroethene, 3.38 g of 4-trifluoromethoxyaniline and 30 ml of ethanol were reacted for 5 hours under heating and refluxing and then cooled to room temperature, whereupon precipitated crystals were collected by filtration and washed with a small amount of ethanol and dried to obtain 3.40 g of crystals, to which 1.81 g of 4-trifluoromethoxyaniline and 30 ml of ethanol were added and reacted for 6.5 hours under heating and refluxing. After completion of the reaction, the solution was cooled to room temperature, and precipitated crystals were collected by filtration, washed with a small amount of ethanol and dried to obtain 2.51 g of N-(1-methylthio-2-nitroethenyl)-4′trifluoromethoxyaniline (Intermediate No. 30) having a melting point of from 114 to 115° C. (2) To 2.00 g of N-(1-methylthio-2-nitroethenyl)-4-trifluoromethoxyaniline (Intermediate No. 30) obtained in the above step (1), 40 ml of ethanol was added at room temperature, and then 0.36 g of hydrazine monohydrate was dropwise added thereto. Thereafter, the reaction was carried out for 1 hour under heating and refluxing. After completion of the reaction, the solution was cooled to room temperature, and precipitated crystals were collected by filtration, washed with a small amount of ethanol and dried to obtain 1.36 g of the desired product (Compound No. 61) having a melting point of 161° C. (decomposition point).

Workup

  1. additionwas added at room temperature
  2. temperatureunder heating
  3. temperaturerefluxing
  4. customAfter completion of the reaction
  5. customprecipitated crystals
  6. filtrationwere collected by filtration
  7. washwashed with a small amount of ethanol
  8. customdried

Sources & evidence

ORD record
ord-5af32fb0c64b4573b754862aa2991ff1
Source dataset
uspto-grants-2002_09
Patent number
US06451792B1

Reaction notes

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