Sodium Chloride → HCID 19901601, compound

HRID 2372689Notes

Reaction equation

C(#N)C.[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH:12][CH:13]=[O:14])=[CH:7][CH:6]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][C:17]=1[N+:26]([O-:28])=[O:27].[Cl-].[Na+]>CN(C)C(=O)C.N1C=CC=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:4][C:5]2[CH:6]=[CH:7][C:8]([NH:11][NH:12][CH:13]=[O:14])=[CH:9][CH:10]=2)(=[O:24])=[O:23])=[CH:18][C:17]=1[N+:26]([O-:28])=[O:27]

Participants

Conditions

Temperature: -5 °C

Procedure

In a mixture of 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 4-chloro-3-nitrobenzenesulfonyl chloride were gradually added to the solution while cooling and 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 was raised to room temperature and the reaction mixture was poured into 1 liter of a saturated aqueous sodium chloride solution. Crystals thus formed were collected by filtration and washed with water to provide 67.5 g of the desired compound.

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 was raised to room temperature
customCrystals thus formed
filtrationwere collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-cc5cfaba45d343ebb24f3e2f4a00dbad
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05100761

Reaction notes

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