Acetonitrile → HCID 178513366, compound

HRID 1685724Notes

Reaction equation

CC#N.[C:4]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH2:16][CH2:17][OH:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)#[N:5].Cl.[NH2:20][OH:21].C([O-])(O)=O.[Na+]>CO>[OH:21][NH:20][C:4](=[NH:5])[C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:13])(=[O:14])[NH:15][CH2:16][CH2:17][OH:18])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-cyano-benzenesulfonyl chloride (1.00 g, 4.96 mmol) in THF, ethanolamine (454 mg, 7.44 mmol) is added. The mixture becomes slightly warm (30° C.) and turbid. The mixture is stirred at rt for 3 h before it is diluted with EA, washed with sat. aq. NH4Cl solution and water, dried over MgSO4, filtered and concentrated to give crude 4-cyano-N-(2-hydroxy-ethyl)-benzenesulfonamide (1.26 g) as a white solid; LC-MS: tR=0.34 min, [M+1+CH3CN]+=268.13. b) A mixture of 4-cyano-N-(2-hydroxy-ethyl)-benzenesulfonamide (1.25 g, 5.56 mmol), hydroxylamine hydrochloride (773 mg, 11.1 mmol) and NaHCO3 (934 mg, 11.1 mmol) in methanol is stirred at 60° C. for 7 h. The mixture is filtered and the filtrate is concentrated. The residue is dissolved in EA (250 mL) and washed with water (5 mL). The organic extract is dried over MgSO4, filtered, concentrated and dried to give the title compound (720 mg) as a white solid; LC-MS: tR=0.23 min.

Workup

filtrationThe mixture is filtered
concentrationthe filtrate is concentrated
dissolutionThe residue is dissolved in EA (250 mL)
washwashed with water (5 mL)
extractionThe organic extract
dry with materialis dried over MgSO4
filtrationfiltered
concentrationconcentrated
customdried

Sources & evidence

ORD record: ord-b8642ba1caab44a780df1e22a1395bfb
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148410B2

Reaction notes

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