Chloride → HCID 19901601, compound

HRID 2372692Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][CH:10]=[O:11])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24].[Cl-]>CN(C)C(=O)C.C(#N)C.N1C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([NH:8][NH:9][CH:10]=[O:11])=[CH:6][CH:7]=2)(=[O:21])=[O:20])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24]

Participants

Conditions

Temperature: -5 °C

Procedure

In 90 ml of N,N-dimethylacetamide, 76 ml of acetonitrile, and 17 ml cf pyridine were dissolved 35.4 g of 2-(4-aminophenyl)-1-formylhydrazine in a nitrogen gas atmosphere and after cooling the solution to -5° C., 59.9 g of 4-chloro-3-nitrobenzenesulfonyl chloride were gradually added to the solution while cooling with stirring so that the liquid temperature was not over -5° C. After further stirring the mixture for 1.5 hours at temperature below -5° C., the temperature was raised to room temperature and the reaciton mixture was poured into 1 liter cf a saturated aqueous solid chloride solution. Crystals formed were collected by filtration and washed with water to provide 67.5 g of the desired product.

Workup

temperaturewhile cooling
customwas not over -5° C
stirringAfter further stirring the mixture for 1.5 hours at temperature below -5° C.
temperaturethe temperature was raised to room temperature
customCrystals formed
filtrationwere collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-b07904b6d4144e5eb5cb66ec64600de2
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05100761

Reaction notes

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