1-Bromo-3-chloropropane → HCID 54350065, compound

HRID 2420331Notes

Reaction equation

HRID 2420331 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([C:11]([CH3:19])=[CH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:20]=1.[OH-].[Na+].Br[CH2:24][CH2:25][CH2:26][Cl:27]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Cl:27][CH2:26][CH2:25][CH2:24][N:9]1[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:20][C:6]=2[N:7]([C:11]([CH3:19])=[CH:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]1=[O:10]

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 538657346-fluoro-1,3-dihydro-1-(1-methyl-2-phenylethenyl)-2H-benzimidazol-2-one

Product 1

HCID 54350065HCID 54350065, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a stirred and hot (50° C) mixture of 15 parts of 6-fluoro-1,3-dihydro-1-(1-methyl-2-phenylethenyl)-2H-benzimidazol-2-one, 3 parts of N,N,N-triethylbenzenemethanaminium chloride and 75 parts of a sodium hydroxide solution 60% are added dropwise 11.1 parts of 1-bromo-3-chloropropane (slightly exothermic reaction). Upon completion, stirring is continued for 4 hours at 60° C. The reaction mixture is cooled, water is added and the product is extracted with methylbenzene. The extract is dried, filtered and evaporated, yielding 20 parts (100%) of 1-(3-chloropropyl)-5-fluoro-1,3-dihydro-3-(1-methyl-2-phenylethenyl)-2H-benzimidazol-2-one as an oily residue.

Workup

  1. customslightly exothermic reaction)
  2. stirringUpon completion, stirring
  3. temperatureThe reaction mixture is cooled
  4. extractionthe product is extracted with methylbenzene
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-206fa47064834c35898d59c900c4f2ac
Source dataset
uspto-grants-1978_08
Patent number
US04110333

Reaction notes

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