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

HRID 133518

Reaction equation

HRID 133518 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][CH:12]=[CH:11][CH:10]=1)=[O:8].[Cl:15]N1C(=O)CCC1=O>ClCCl>[NH2:1][C:2]1[S:3][C:4]([Cl:15])=[CH:5][C:6]=1[C:7]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:8]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 644720(2-Aminothiophen-3-yl)(phenyl)methanone

Product 1

HCID 16640283(2-Amino-5-chloro-thiophen-3-yl)-phenyl-methanoneYield 34.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.1 g (0.49 mmol) (2-amino-thiophen-3-yl)-phenyl-methanone (the preparation of which is described in example 20) in 10 ml dichloromethane at 0° C. was added 68 mg (0.49 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 concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 3:1) afforded 40 mg (34%) (2-amino-5-chloro-thiophen-3-yl)-phenyl-methanone as a yellow solid.

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
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b0249afe0124d84a66e978ce26a7cde
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Linked notes

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