Hydrazine, dihydrochloride → HCID 58772595, compound

HRID 2250351Notes

Reaction equation

HRID 2250351 reaction equation
Cl.Cl.[NH2:3][NH2:4].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13](=O)[O:14][C:15](=[O:17])[CH:16]=2)=[CH:8][CH:7]=1>O>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13](=[O:14])[NH:3][NH:4][C:15](=[O:17])[CH:16]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 17548Hydrazine, dihydrochlorideHCID 5859973-(4-Chlorophenyl)-2,5-furandione

Product 1

HCID 58772595HCID 58772595, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of hydrazine dihydrochloride (5.6 g, 53.3 mmol) in H2O (60 mL) at 120° C. was added 3-(4-chlorophenyl)-2,5-furandione (10 g, 48 mmol) in one portion. After addition, the reaction mixture was stirred at 120° C. for 40 min. After cooling to room temperature, the reaction became a pale yellow suspension. The precipitate was collected by filtration, washed with water (30 mL×3), hexanes (30 mL×3), and dried in a 50° C. vacuum oven for 16 h to afford 8.7 g (81%) of the title compound as a pale yellow solid. LC/MS (method A): retention time=2.57 min, (M+H)+=223.

Workup

  1. additionAfter addition
  2. temperatureAfter cooling to room temperature
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water (30 mL×3), hexanes (30 mL×3)
  5. customdried in a 50° C. vacuum oven for 16 h

Sources & evidence

ORD record
ord-cf9b74dc4f72487c90c8c0e99b9d3b4a
Source dataset
uspto-grants-2008_01
Patent number
US07317012B2

Reaction notes

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