N-bromobutanimide → HCID 67158605, compound

HRID 549359Notes

Reaction equation

HRID 549359 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH:17]2[CH2:22][C:23]2[O:24][CH:25]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:27]=2)=[O:15])=[CH:4][CH:3]=1.[Br:34]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:34][C:25]1[O:24][C:23]([CH2:22][CH:17]2[CH2:18][O:19][CH2:20][CH2:21][N:16]2[C:14]([C:9]2[N:10]=[C:11]([CH3:13])[S:12][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:15])=[N:27][C:26]=1[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 67157836HCID 67157836, compound

Product 1

HCID 67158605HCID 67158605, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The compound of example 67 (0.152 g) was dissolved in carbon tetrachloride (10 ml) and was then treated with N-bromosuccinimide (0.058 g) and stirred under argon at room temperature for 24 h. A further quantity of N-bromosuccinimide (0.006 g) was added and the mixture stirred for a further 1 h. The mixture was filtered through a cotton wool plug and the filtrate was evaporated to dryness under reduced pressure. The residue was column chromatographed (silica gel, 0→40% ethyl acetate-pentane) to give the title compound (0.117 g).

Workup

  1. stirringthe mixture stirred for a further 1 h
  2. filtrationThe mixture was filtered through a cotton wool plug
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. customchromatographed (silica gel, 0→40% ethyl acetate-pentane)

Sources & evidence

ORD record
ord-66357586203a4229a5c123d207e6a878
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

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