N-bromobutanimide → HCID 54255534, compound

HRID 1368269Notes

Reaction equation

HRID 1368269 reaction equation
[CH3:1][N:2]([CH:4]=[N:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])(=[O:8])=[O:7])[CH3:3].C1C(=O)N([Br:32])C(=O)C1>ClC1C=CC=CC=1.C1(C)C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:32][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([S:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:6]([N:5]=[CH:4][N:2]([CH3:1])[CH3:3])(=[O:7])=[O:8])(=[O:16])=[O:17])=[CH:23][CH:22]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 54092854HCID 54092854, compound

Product 1

HCID 54255534HCID 54255534, compoundYield 87.8%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 1140TolueneSolventHCID 7964ChlorobenzeneSolvent

Procedure

1.5 g of N-dimethylaminomethylene-2-(toluene-4-sulfonyl)benzenesulfonamide, 0.74 g of NBS and 20 mg of benzoyl peroxide are refluxed for 2 h in 15 ml of chlorobenzene. The reaction mixture is allowed to cool and is diluted with 100 ml of toluene, and washed once each with 20 ml of a saturated aqueous Na2SO3 solution and twice with 50 ml of a saturated aqueous Na2CO3 solution. It is dried over MgSO4 and the solvent is removed in vacuo. 1.6 g of an amorphous solid are obtained, which is further reacted without further purification.

Workup

  1. temperatureto cool
  2. washwashed once each with 20 ml of a saturated aqueous Na2SO3 solution
  3. dry with materialIt is dried over MgSO4
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-e633d300c3dc43e59456b3cc5c80ea43
Source dataset
uspto-grants-2003_06
Patent number
US06573288B1

Reaction notes

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