Hydroxylamine → N-hydroxy-4-[2-(benzofuran-2-ylcarbonylamino)-ethylsulfanyl]benzamide

HRID 1173809Notes

Reaction equation

HRID 1173809 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][CH2:13][CH2:14][S:15][C:16]1[CH:25]=[CH:24][C:19]([C:20](OC)=[O:21])=[CH:18][CH:17]=1)=[O:11].[NH2:26][OH:27].CO.[OH-].[Na+]>C1COCC1.O>[OH:27][NH:26][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][C:16]([S:15][CH2:14][CH2:13][NH:12][C:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)=[O:11])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 887MethanolHCID 14798Sodium HydroxideHCID 66687946Methyl 4-{2-[(benzofuran-2-yl-carbonyl)amino]ethylsulfanyl}benzoate

Product 1

HCID 58975601N-hydroxy-4-[2-(benzofuran-2-ylcarbonylamino)-ethylsulfanyl]benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-{2-[(benzofuran-2-yl-carbonyl)amino]ethylsulfanyl}-benzoate in THF (2 ml) was added a solution of 50% hydroxylamine in water (4 ml). Methanol (2 ml) and 0.1 M NaOH (0.1 ml) were added. The reaction mixture was stirred for three days at room temperature. The solvents were evaporated and the residue was crystallized from dichloromethane/ethyl acetate, to give the title compound (46 mg).

Workup

  1. customThe solvents were evaporated
  2. customthe residue was crystallized from dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-fb1487d3bb564f53b1a692eade88ad82
Source dataset
uspto-grants-2010_11
Patent number
US07834054B2

Reaction notes

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