Sodium Chloride → HCID 19901598, compound

HRID 2372691Notes

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]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=1[S:22](Cl)(=[O:24])=[O:23].[Cl-].[Na+]>CN(C)C(=O)C.C(#N)C.N1C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=1[S:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][CH:10]=[O:11])=[CH:6][CH:7]=1)(=[O:24])=[O:23]

Participants

Conditions

Temperature: -5 °C

Procedure

In 90 ml of N,N-dimethylacetamide, 76 ml of acetonitrile, and 19 ml of 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 2-chloro-5-nitrobenzenesulfonyl chloride was gradually added thereto while cooling with stirring so that the liquid temperature was not over -5° C. After further stirring the mixture for 1.5 hours at a temperature below -5° C., the temperature thereof was raised to room temperature and the reaction mixture was poured into 1 liter of a saturated aqueous sodium chloride solution. Crystals formed were collected by filtration and washed with water to provide 63 g of the desired product.

Workup

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

Sources & evidence

ORD record: ord-0865611216df40ccb77595913f84b573
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05100761

Reaction notes

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