Ethanethiol → HCID 53773181, compound

HRID 2209743Notes

Reaction equation

[NH2:1][C:2](=[N:33][OH:34])[C:3]1[CH:32]=[CH:31][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:28]=[CH:27][C:17]([C:18]([N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:16][C:15]=2[O:29]C)=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(S)C>ClCCl>[NH2:1][C:2](=[N:33][OH:34])[C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:28]=[CH:27][C:17]([C:18]([N:20]([CH:24]([CH3:25])[CH3:26])[CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:16][C:15]=2[OH:29])=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of 4-[5-[4-[amino(hydroxyimino)methyl]phenoxy]pentyloxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide (200 mg, 0.4 mmol) in 4 mL of dichloromethane at 0° C. is treated with aluminum chloride (292 mg, 2.2 mmol) and ethanethiol (4 mL, 54 mmol). After stirring at 0° C. for 1 hour, reaction mixture is partitioned between ethyl acetate and saturated ammonium hydroxide solution. The organic phase is dried with magnesium sulfate and concentrated in vacuo. The resulting material is purified by chromatography on silica gel (10 g) with 5% methanol/dichloromethane as the eluent to afford 4-[5-[4-[amino(hydroxyimino)methyl]phenoxy]pentyloxy]-3-hydroxy-N,N-bis(1-methylethyl)benzamide as a colorless foam;

Workup

customreaction mixture
customis partitioned between ethyl acetate and saturated ammonium hydroxide solution
dry with materialThe organic phase is dried with magnesium sulfate
concentrationconcentrated in vacuo
customThe resulting material is purified by chromatography on silica gel (10 g) with 5% methanol/dichloromethane as the eluent

Sources & evidence

ORD record: ord-b307404923a6487c9ac54884e55b9df3
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455274

Reaction notes

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