Hydrochloric Acid → n-(3-Bromo-5-phenylsulphanylphenyl)-n-methylacetamide

HRID 1603616Notes

Reaction equation

N[C:2]1[CH:3]=[C:4]([N:9]([CH3:13])[C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Br:8])[CH:7]=1.Cl.N([O-])=O.[Na+].[Na].[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[Br:8][C:6]1[CH:5]=[C:4]([N:9]([CH3:13])[C:10](=[O:12])[CH3:11])[CH:3]=[C:2]([S:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

0.243 g (0.001 mol) of N-(3-amino-5-bromophenyl)-N-methylacetamide was suspended in 5 ml of water, treated with 0.2 ml (0.002 mol) of HCl (37%) and cooled to 0° C. A solution of 0.069 g (0.001 mol) of NaNO2 in 1 ml of water was added thereto, the mixture was stirred at 0° C. for 5 min. and subsequently at room temperature for 10 min. and finally treated with a suspension of 0.35 g (0.0025 mol) of thiophenol sodium salt. The reaction mixture was treated in an ultrasound bath for 10 min. and subsequently partitioned in water/ethyl acetate. The organic phase was washed with sat. sodium chloride solution, dried over MgSO4 filtered and freed from solvent. The residue was then heated to 120-130° C. for 20 min., taken up in ethyl acetate and chromatographed on silica gel with ethyl acetate/hexane 1:9 and 1:2. There was obtained 0.085 g (21%) of N-(3-bromo-5-phenylsulphanylphenyl)-N-methylacetamide as a yellow oil. MS (EI): me/e=337, 335 (C15H14BrNOS+).

Workup

additionThe reaction mixture was treated in an ultrasound bath for 10 min.
customsubsequently partitioned in water/ethyl acetate
washThe organic phase was washed with sat. sodium chloride solution
dry with materialdried over MgSO4
filtrationfiltered
temperatureThe residue was then heated to 120-130° C. for 20 min.
customchromatographed on silica gel with ethyl acetate/hexane 1:9 and 1:2

Sources & evidence

ORD record: ord-75273df2e95347658737e33e5e0b13d8
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990105

Reaction notes

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