N-bromobutanimide → HCID 18923362, compound

HRID 1899971Notes

Reaction equation

HRID 1899971 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[S:10][C:6]=2[CH:5]=[C:4]([Cl:13])[C:3]=1[CH3:14].[Br:15]N1C(=O)CCC1=O>N(C(C)(CC(C)(OC)C)C#N)=NC(C)(CC(OC)(C)C)C#N.ClCCl>[Br:15][CH2:14][C:3]1[C:4]([Cl:13])=[CH:5][C:6]2[S:10][C:9](=[O:11])[N:8]([CH3:12])[C:7]=2[C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 18923332HCID 18923332, compound

Product 1

HCID 18923362HCID 18923362, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 858672,2'-Azobis(2,4-dimethyl-4-methoxyvaleronitrile)CatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4,6-dichloro-3,5-dimethyl-2-benzothiazolinone (1.30 g), N-bromosuccinimide (1.03 g), 2,2'-azobis-(2,4-dimethyl-4-methoxyvaleronitrile) (65 mg) and dichloromethane (26 ml) was heated under reflux for 2 hours. N-Bromosuccinimide (500 mg) was added therein and the mixture was heated under reflux for additional 4 hours. The reaction mixture was washed with water twice and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from diethyl ether to give 5-bromomethyl-4,6-dichloro-3-methyl-2-benzothiazolinone (1.20 g) as crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for additional 4 hours
  5. washThe reaction mixture was washed with water twice
  6. dry with materialbrine, dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-9a1ad725939e4254a726787fba0857fb
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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