Sodium Chloride → 2-Ethylthio-4,5-bis-(p-methoxyphenyl)-thiazole

HRID 544649Notes

Reaction equation

HRID 544649 reaction equation
[CH2:1]([SH:3])[CH3:2].[H-].[Na+].Cl[C:7]1[S:8][C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:11]=1.[Cl-].[Na+]>CN(C)P(=O)(N(C)C)N(C)C>[CH2:1]([S:3][C:7]1[S:8][C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[N:11]=1)[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 197579572-Chloro-4,5-bis-(p-methoxyphenyl)-thiazole

Product 1

HCID 132096692-Ethylthio-4,5-bis-(p-methoxyphenyl)-thiazole

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

0.217 g of ethyl mercaptan is dissolved under nitrogen in 10 ml of hexamethylphosphoric acid triamide, the solution is cooled to 10° and, while stirring, 170 mg of 50% strength sodium hydride suspension (in mineral oil, de-oiled with hexane) are added in portions. The mixture is then stirred for 15 minutes at room temperature, 1.0 g of 2-chloro-4,5-bis-(p-methoxyphenyl)-thiazole is added and stirring is carried out at room temperature for 1 hour. The mixture is then poured into 300 ml of 10% strength sodium chloride solution, digested until crystallisation occurs and filtered with suction and the residue is then washed twice with water and sucked dry on a suction filter. The crude product is recrystallised from methanol. 2-Ethylthio-4,5-bis-(p-methoxyphenyl)-thiazole having a melting point of 73°-75° is obtained.

Workup

  1. temperaturethe solution is cooled to 10°
  2. stirringThe mixture is then stirred for 15 minutes at room temperature
  3. stirringstirring
  4. customdigested until crystallisation
  5. filtrationfiltered with suction
  6. washthe residue is then washed twice with water
  7. customsucked dry on a suction
  8. filtrationfilter
  9. customThe crude product is recrystallised from methanol

Sources & evidence

ORD record
ord-bf280a3f8d8941239a4aa248254c872e
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

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