Sodium hydride → Tert-butyl 4-[(2-amino-1,1-dimethylethyl)thio]benzoate

HRID 131297Notes

Reaction equation

HRID 131297 reaction equation
Cl.[NH2:2][CH2:3][C:4]([CH3:7])([SH:6])[CH3:5].[H-].[Na+].F[C:11]1[CH:23]=[CH:22][C:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:13][CH:12]=1>CN(C)C=O.O>[NH2:2][CH2:3][C:4]([S:6][C:11]1[CH:23]=[CH:22][C:14]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[CH:13][CH:12]=1)([CH3:7])[CH3:5]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2736444Tert-butyl 4-fluorobenzoateHCID 130491041-Amino-2-methyl-2-propanethiol hydrochloride

Product 1

HCID 69301223Tert-butyl 4-[(2-amino-1,1-dimethylethyl)thio]benzoateYield 75.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1-amino-2-methyl-2-propanethiol hydrochloride (75 mg) in N,N-dimethylformamide (2 mL) is added sodium hydride (60% dispersion in mineral oil, 50 mg) and the mixture is stirred at room temperature for 30 minutes. To the mixture is added tert-butyl 4-fluorobenzoate (50 mg) and the mixture is stirred at 70° C. for 4 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is concentrated in vacuo and the resultant product is purified by flash column chromatography on NH-silica gel (solvent; ethyl acetate) to give tert-butyl 4-[(2-amino-1,1-dimethylethyl)thio]benzoate (54 mg, yield; 75%) as a colorless oil. MS (APCI) m/z: 282 [M+H]+

Workup

  1. stirringthe mixture is stirred at 70° C. for 4 hours
  2. extractionextracted with ethyl acetate
  3. concentrationThe extract is concentrated in vacuo
  4. customthe resultant product is purified by flash column chromatography on NH-silica gel (solvent; ethyl acetate)

Sources & evidence

ORD record
ord-a4326f640f3a4f4ca506856327a301d3
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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