N-bromobutanimide → HCID 67613748, compound

HRID 1734633Notes

Reaction equation

HRID 1734633 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([O:12][CH:13]1[CH2:17][CH:16]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[CH2:15][CH:14]1[N:23]1[C:27]2[CH:28]=[C:29]([Cl:33])[C:30]([Cl:32])=[CH:31][C:26]=2[N:25]=[CH:24]1)(=[O:11])[CH3:10]>CN(C)C=O>[C:9]([O:12][CH:13]1[CH2:17][CH:16]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[CH2:15][CH:14]1[N:23]1[C:27]2[CH:28]=[C:29]([Cl:33])[C:30]([Cl:32])=[CH:31][C:26]=2[N:25]=[C:24]1[Br:1])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 23198916HCID 23198916, compound

Product 1

HCID 67613748HCID 67613748, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

N-Bromosuccinimide (4.54 g, 25.5 mmol) was added to a solution of (±)-(1R*, 2R*, 4S*)-4-(acetoxymethyl)-2-(5,6-dichloro-1H-benzimidazol-1-yl)cyclopentyl acetate (8.95 g, 23.2 mmol) in dry N,N-dimethylformamide (46 mL). The solution was maintained at ca. 70° C. (oil bath) for 5 hours. Volatiles were removed in vacuo and the residual orange syrup chromatographed on silica gel. Title compound was eluted with chloroform as a pale yellow solid (5.14 g, 48%), m.p. 122°-125° C.; 1H-NMR (DMSO-d6)δ: 8.16 (s, 1, benzimidazole H7), 7.95 (s, 1, benzimidazole H4), 5.60-5.55 (m, 1, OCH), 5.12-5.03 (m, 1, NCH), 4.15 (d, J=6.3 Hz, 2, OCH2), 2.66-2.60 (m, 1, CHCH2), 2.29-2.14 (m, 3, CH), 2.06 (s, 3, CH3CO), 1.93 (s overlapped by m, 4, CH3CO+CH); mass spectrum (CI): 469 (5.8), 467 (37.5), 465 (95), 463 (54, M+1), 199 (100, M-B).

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residual orange syrup chromatographed on silica gel
  3. washTitle compound was eluted with chloroform as a pale yellow solid (5.14 g, 48%), m.p. 122°-125° C.

Sources & evidence

ORD record
ord-94acf066485f4235aa90277f55812506
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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