Sodium Hydroxide → HCID 53655731, compound

HRID 258837Notes

Reaction equation

HRID 258837 reaction equation
[CH3:1][C:2]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19])=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].Br[CH2:23][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][CH2:23][N:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:10]([C:2]([CH3:1])=[CH:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:11]1=[O:19]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 813641-Bromo-4-chlorobutaneHCID 54397327HCID 54397327, compound

Product 1

HCID 53655731HCID 53655731, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 38.5 parts of 1,3-dihydro-1-(1-methyl-2-phenylethenyl)-2H-benzimidazol-2-one, 5 parts of N,N,N-triethylbenzenemethanaminium chloride and 225 parts of sodium hydroxide solution 60% is stirred and heated at 55° C. Then there are added dropwise 30.9 parts of 1-bromo-4-chlorobutane. Upon completion, stirring at 55° C is continued for 4 hours. The reaction mixture is cooled, water is added and the oily product is extracted with methylbenzene. The extract is dried, filtered and evaporated, yielding 53 parts of 1-(4-chlorobutyl)-1,3-dihydro-3-(1-methyl-2-phenylethenyl)-2H-benzimidazol-2-one as a residue.

Workup

  1. stirringUpon completion, stirring at 55° C
  2. temperatureThe reaction mixture is cooled
  3. extractionthe oily product is extracted with methylbenzene
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-85774473bb454686971f1b2ec9140755
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Reaction notes

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