N-bromobutanimide → HCID 59457457, compound

HRID 1710780Notes

Reaction equation

HRID 1710780 reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][Cl:18])=[CH:10][CH:9]=2)[O:6][CH:7]=1.[Br:19]N1C(=O)CCC1=O>C(#N)C>[Br:19][C:7]1[O:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][Cl:18])=[CH:12][CH:13]=2)=[N:4][C:3]=1[CH2:2][Cl:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59457464HCID 59457464, compound

Product 1

HCID 59457457HCID 59457457, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(chloromethyl)-2-[4-(3-chloropropoxy)phenyl]-1,3-oxazole ax57 (0.5 g, 1.75 mmol, 1 eq) and N-bromosuccinimide (0.31 g, 1.75 mmol, 1 eq) in acetonitrile (16 ml) is stirred at 22° C. for 30 minutes. A heavy white precipitate forms during the reaction. The suspension is then filtered, the solid is washed with the minimum amount acetonitrile, collected and dried under vacuum at 40° C. to yield 290 mg of the title compound. The acetonitrile solution is concentrated to half its original volume to yield an additional 110 mg of 5-bromo-2-[4-(3-chloropropoxy)-phenyl]-4-chloromethyl-oxazole i89.

Workup

  1. customA heavy white precipitate forms during the reaction
  2. filtrationThe suspension is then filtered
  3. washthe solid is washed with the minimum amount acetonitrile
  4. customcollected
  5. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-de024011d31a49c3890efbea1e4e4a3e
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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