Hydroxylamine → HCID 58121147, compound

HRID 1186698Notes

Reaction equation

HRID 1186698 reaction equation
[C:1]1([C:7]2[S:8][C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:10][C:11]=2[C:12](OCC)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:23][OH:24].O>CO.C1COCC1>[OH:24][NH:23][C:12]([C:11]1[CH:10]=[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:8][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:13]

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 12477826HCID 12477826, compound

Product 1

HCID 58121147HCID 58121147, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of ethyl 2,5-diphenylthiophene-3-carboxylate 70 (0.440 g, 1.427 mmol) in methanol (7 mL) and THF (7 mL) was added 50% hydroxylamine in water (1.4 mL, 23.31 mmol) and the resulting mixture was stirred at room temperature for 45 minutes then concentrated to one third volume. The solution was neutralized with 3N HCl to pH 7 and the desired product was filtered then purified by Gilson (55 to 95% MeOH in H2O) to afford the title compound 71 (87 mg, 21% yield) as a white solid. 1H NMR: (DMSO-d6) d(ppm) 1H, 10.96 (s, 1H), 9.14 (s, 1H), 7.71-7.69 (m, 2H), 7.57-7.55 (m, 3H), 7.48-7.34 (m, 6H) LRMS (ESI): (calc) 295.36 (found) 296.22 (MH)+

Workup

  1. concentrationthen concentrated to one third volume
  2. filtrationthe desired product was filtered
  3. customthen purified by Gilson (55 to 95% MeOH in H2O)

Sources & evidence

ORD record
ord-15c900612c5e4e5c916c9c6eaf533f2a
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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