Hydroxyamine hydrochloride → HCID 5353765, compound

HRID 226186Notes

Reaction equation

HRID 226186 reaction equation
Cl.[NH2:2][OH:3].[C:4]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]=[CH:21][C:22](Cl)=[O:23])=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1>O1CCCC1>[OH:3][NH:2][C:22](=[O:23])/[CH:21]=[CH:20]/[C:17]1[CH:18]=[CH:19][C:14]([NH:13][S:10]([C:7]2[CH:8]=[CH:9][C:4]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:5][CH:6]=2)(=[O:12])=[O:11])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 73989395HCID 73989395, compound

Product 1

HCID 5353765HCID 5353765, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of hydroxylamine hydrochloride (0.27 g, 3.88 mmol) in tetrahydrofuran (5 ml) saturated NaHCO3 solution (3 ml) was added and the resultant mixture was stirred at ambient temperature for 10 min. To the reaction mixture a solution of crude 3-[3-(3-methoxy-phenylsulfamoyl)-phenyl]-acryloyl chloride (83a) (0.27 g, 0.68 mmol) in tetrahydrofuran (3.5 ml) was added and the mixture was stirred at ambient temperature for one hour. The reaction mixture was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water and saturated NaCl, then the solvent was removed. The residue was crystallised from acetonitrile and washed with diethyl ether affording the title compound as a white solid (0.1 g, 37%). M.p. 190-191.5° C. 1H NMR (DMSO-d6, HMDSO) δ: 6.29 (1H, d, J=16.0 Hz); 7.16 (2H, d, J=8.0 Hz); 7.24-7.78 (8H, m); 7.86 (4H, m); 8.94 (1H, br s); 10.57 (1H, s); 10.66 (1H, br s). HPLC analysis on Zorbax SB-C18 column: impurities 4% (column size 4.6×150 mm; mobile phase acetonitrile—0.1% H3PO4F gradient from 30 to 100%; sample concentration 0.2 mg/ml; flow rate 1.0 ml/min; detector UV 254 nm). Anal. Calcd for C21H18N2O4S, %: C 63.94, H 4.60, N 7.10. Found, %: C C 63.64, H 4.45, N 7.00.

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between ethyl acetate and 2N HCl
  3. washThe organic layer was washed successively with water and saturated NaCl
  4. customthe solvent was removed
  5. customThe residue was crystallised from acetonitrile
  6. washwashed with diethyl ether affording the title compound as a white solid (0.1 g, 37%)

Sources & evidence

ORD record
ord-d0dee23046f34863ae04eb8772e46d83
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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