N-bromobutanimide → HCID 19858577, compound

HRID 2072594Notes

Reaction equation

HRID 2072594 reaction equation
C(=O)=O.CC(C)=O.[C:8]([S:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)([CH3:11])([CH3:10])[CH3:9].[Br:20]N1C(=O)CCC1=O>C(Cl)Cl>[C:8]([S:12][C:13]1[CH:14]=[CH:15][C:16]([NH2:17])=[C:18]([Br:20])[CH:19]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 109101774-(tert-butylsulfanyl)anilineHCID 18522661Acetone cardice

Product 1

HCID 19858577HCID 19858577, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold (dry ice - acetone bath) stirred solution of 4-tert-butylthioaniline (25.6 g., 0.14 mole) in methylene chloride is added a slurry of N-bromosuccinimide (25.0 g., 0.14 mole) in methylene chloride in three equal portions. The reaction is allowed to come to room temperature with stirring overnight. The methylene chloride solution is washed with dilute aqueous sodium carbonate and water and then evaporated to give the desired product as a brown oil.

Workup

  1. customto come to room temperature
  2. washThe methylene chloride solution is washed with dilute aqueous sodium carbonate and water
  3. customevaporated

Sources & evidence

ORD record
ord-dcc08a60178d45f3a0ea7038e57a7b88
Source dataset
uspto-grants-1990_04
Patent number
US04913728

Reaction notes

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