N-bromobutanimide → HCID 86585504, compound

HRID 1281690Notes

Reaction equation

HRID 1281690 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([N:11]2[C:15]3[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=3[N:13]=[CH:12]2)[C@@H:6]1[O:22][C:23](=[O:25])[CH3:24])(=[O:3])[CH3:2].[Br:26]N1C(=O)CCC1=O>CN(C)C=O>[C:1]([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([N:11]2[C:15]3[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=3[N:13]=[C:12]2[Br:26])[C@@H:6]1[O:22][C:23](=[O:25])[CH3:24])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 131723497HCID 131723497, compound

Product 1

HCID 86585504HCID 86585504, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(±)-(1R*,2S*,3R*)-3-(5,6-Dichloro-1H-benzimidazol-1-yl)-1,2-cyclohexanediyl diacetate (part b of this example, 1.58 g, 4.10 mmol) was dissolved in dry N,N-dimethylformamide (6.4 ml) and maintained at 65° C. under nitrogen while N-bromosuccinimide (1.46 g, 8.2 mmol) was added in 2 portions over 1 h. Volatiles were evaporated in vacuo and the residue was chromatographed on silica gel. Title compound was eluted with ethyl acetate as an off-white powder (0.95 g, 49%), m.p. 71-79° C.

Workup

  1. additionwas added in 2 portions over 1 h
  2. customVolatiles were evaporated in vacuo
  3. customthe residue was chromatographed on silica gel
  4. washTitle compound was eluted with ethyl acetate as an off-white powder (0.95 g, 49%), m.p. 71-79° C.

Sources & evidence

ORD record
ord-ebe670a650044aa58ef63ed934ab706c
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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