Acetic Acid → HCID 131724703, compound

HRID 1760254Notes

Reaction equation

HRID 1760254 reaction equation
[Br:1]N1C(=O)CCC1=O.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH:14]([O:20][C:21](=[O:23])[NH2:22])[CH2:15][C:16]([N:18]=[O:19])=[O:17].C(Cl)(Cl)Cl.C(O)(=O)C>O>[Br:1][C:13]1[S:9][C:10]([CH:14]([O:20][C:21](=[O:23])[NH2:22])[CH2:15][C:16]([N:18]=[O:19])=[O:17])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 67184N-bromobutanimideHCID 131724704HCID 131724704, compound

Product 1

HCID 131724703HCID 131724703, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-bromosuccinimide (1.79 g) was added in portions to a solution of (±)-(2-(2-thienyl)-2-carbamoyloxyethyl)oxocarboxamide (2.2 g 9.5 mmol) in 40 ml of a 1:1 mixture of chloroform and acetic acid. The resulting suspension was stirred for 24 hours. The reaction mixture was then diluted with an equal volume of water and the separated organic layer was recovered, and sequentially washed with potassium hydroxide solution and water. The extracts were dried over sodium sulfate, filtered, concentrated and purified by recrystallization from dichloromethane to yield the title compound as a white solid (2.2 g). M.p. 160-161° (from dichloromethane).

Workup

  1. customthe separated organic layer was recovered
  2. washsequentially washed with potassium hydroxide solution and water
  3. dry with materialThe extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by recrystallization from dichloromethane

Sources & evidence

ORD record
ord-b5da4e45e7db4ce8a3605148458da149
Source dataset
uspto-grants-2005_01
Patent number
US06841569B2

Reaction notes

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