Potassium Hydroxide → HCID 14374020, compound

HRID 2352569Notes

Reaction equation

HRID 2352569 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[O:11])=[CH:6][CH:5]=1.[CH3:21][N:22]([CH3:26])[C:23](Cl)=[S:24]>O.O1CCCC1.[OH-].[Na+]>[CH3:21][N:22]([CH3:26])[C:23](=[S:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:11])[C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 27871Dimethylthiocarbamoyl chlorideHCID 110968174-Hydroxy-4'-nitrobenzophenone

Product 1

HCID 14374020HCID 14374020, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

1.4 g (0.025 mol) of potassium hydroxide pellets are added to a suspension of 5.4 g (0.0224 mol) of 4-hydroxyphenyl 4-nitrophenyl methanone in 60 ml of water. The reaction mixture is heated at 50° C. for two hours, with vigorous stirring. The mixture is then cooled to 0° C. and a solution of 3.5 g (0.029 mol) of dimethylthiocarbamoyl chloride in 15 ml of tetrahydrofuran (THF) is added dropwise. When the addition is complete, the reaction mixture is stirred for 15 minutes at 0° C. and then for one hour at 20° C. The reaction medium is then hydrolyzed in 25 ml of 1N NaOH at 0° C. The precipitate obtained is filtered off and washed with water until the pH of the washings is neutral. After drying, it is recrystallized from a methylene chloride/hexane mixture to give 5.9 g (yield: 84%) of the expected product melting at 168° C.

Workup

  1. temperatureThe mixture is then cooled to 0° C.
  2. additionWhen the addition
  3. waitfor one hour at 20° C
  4. customat 0° C
  5. customThe precipitate obtained
  6. filtrationis filtered off
  7. washwashed with water until the pH of the washings
  8. customAfter drying
  9. customit is recrystallized from a methylene chloride/hexane mixture

Sources & evidence

ORD record
ord-de3380ac43154974923000d816d34e46
Source dataset
uspto-grants-1989_10
Patent number
US04877808

Reaction notes

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