Chlorosuccinimide → (2-Amino-5-chloro-thiophen-3-yl)-(4-fluoro-phenyl)-methanone

HRID 133525Notes

Reaction equation

HRID 133525 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:8].[Cl:16]N1C(=O)CCC1=O>ClCCl>[NH2:1][C:2]1[S:3][C:4]([Cl:16])=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11074943(2-Aminothiophen-3-YL)(4-fluorophenyl)methanone

Product 1

HCID 68896462(2-Amino-5-chloro-thiophen-3-yl)-(4-fluoro-phenyl)-methanoneYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.26 g (1.18 mmol) (2-amino-thiophen-3-yl)-(4-fluoro-phenyl)-methanone (the preparation of which is described in example 22) in 10 ml dichloromethane at 0° C. was added 164 mg (1.18 mmol) N-chloro-succinimide (NCS). The mixture was then stirred from 0° C. to RT over night, and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentratedin vacuo. Flash chromatography (heptane/ethyl acetate 4:1) afforded 95 mg (32%) (2-amino-5-chloro-thiophen-3-yl)-(4-fluoro-phenyl)-methanone as a yellow solid. ES-MS m/e (%): 256 (M+H+, 100).

Workup

  1. customat 0° C.
  2. additionpoured onto water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate and concentratedin vacuo

Sources & evidence

ORD record
ord-c4b71c3c697a4db682b15b9da0cf0274
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

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