N-bromobutanimide → HCID 67125229, compound

HRID 874187Notes

Reaction equation

HRID 874187 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH3:17])[S:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14].[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:17][C:10]1[S:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86660450HCID 86660450, compound

Product 1

HCID 67125229HCID 67125229, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5.00 g (18.6 mmol) of methyl 4-(2-chlorophenyl)-2-methyl-1,3-thiazole-5-carboxylate and 3.38 g (19.0 mmol) of N-bromosuccinimide were dissolved in 100 ml of carbon tetrachloride and, with stirring, heated to the boil. At boiling point, 170 mg (1.00 mmol) of 2,2′-azobis-2-methylpropionitrile were added a little at a time over a period of 5 hours, followed by refluxing for a further hour. After cooling to room temperature, the reaction solution was filtered and the mother liquor was freed from the solvent under reduced pressure. The desired product was isolated by chromatographic purification.

Workup

  1. temperatureheated to the boil
  2. additionwere added a little at a time over a period of 5 hours
  3. temperatureby refluxing for a further hour
  4. filtrationthe reaction solution was filtered

Sources & evidence

ORD record
ord-21533b6f4c734816b9b2ab9a4f777c94
Source dataset
uspto-grants-2015_03
Patent number
US08980886B2

Reaction notes

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