Potassium Hydroxide → HCID 13284561, compound

HRID 1981250Notes

Reaction equation

HRID 1981250 reaction equation
Cl[CH2:2][CH:3]([CH3:12])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:13][S:14][C:15]1[CH:16]=[C:17]([N:21]=[C:22]=[O:23])[CH:18]=[CH:19][CH:20]=1.[OH-].[K+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:12][CH:3]1[CH2:2][N:21]([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([S:14][CH3:13])[CH:16]=2)[C:22](=[O:23])[N:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:4]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 1414183-(Methylthio)phenyl isocyanateHCID 13284549N-(3-chloro-2-methylpropyl)aniline

Product 1

HCID 13284561HCID 13284561, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

18.4 g of N-(3-chloro-2-methylpropyl)aniline was dissolved in 120 ml of toluene, and 16.5 g of 3-methylthiophenyl isocyanate was added at room temperature. Then, the mixture was stirred at 40° to 50° C. for 1 hour. A catalytic amount (0.2 g) of tetrabutyl ammonium bromide was then added. While maintaining the temperature of the mixture at 30° to 40° C., 34 g of a 50% by weight aqueous solution of potassium hydroxide was added dropwise to the mixture. After the addition, the mixture was well stirred at 40° to 50° C. for 1 hour to complete the reaction. The reaction mixture was cooled to room temperature. The toluene layer was separated and washed with 1% by weight HCl and water in this order. After dehydration, the toluene was distilled off under reduced pressure to give 20.3 g of the desired 5-methyl-1-(3-methylthiophenyl)-3-phenyl-tetrahydro-2-pyrimidinone as a viscous pale yellow liquid. nD20 1.6194

Workup

  1. temperatureWhile maintaining the temperature of the mixture at 30° to 40° C.
  2. additionAfter the addition
  3. stirringthe mixture was well stirred at 40° to 50° C. for 1 hour
  4. customthe reaction
  5. customThe toluene layer was separated
  6. washwashed with 1% by weight HCl and water in this order
  7. distillationAfter dehydration, the toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-20c6042527224a6f9dd9f43cff442320
Source dataset
uspto-grants-1985_04
Patent number
US04514210

Reaction notes

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