Chloroform → HCID 13849380, compound

HRID 2309361Notes

Reaction equation

HRID 2309361 reaction equation
[CH3:1][C:2]1[S:22][C:5]2[N:6]=[C:7]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[N:8]=[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1.[F:23][C:24]1[CH:33]=[CH:32][C:27]([C:28](=[O:31])[CH2:29]Cl)=[CH:26][CH:25]=1.C(N(CC)CC)C.C(Cl)(Cl)Cl>CC(CC)=O>[F:23][C:24]1[CH:33]=[CH:32][C:27]([C:28](=[O:31])[CH2:29][N:19]2[CH2:20][CH2:21][N:16]([C:7]3[N:8]=[C:9]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:4]4[CH:3]=[C:2]([CH3:1])[S:22][C:5]=4[N:6]=3)[CH2:17][CH2:18]2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 1202482-Chloro-4'-fluoroacetophenoneHCID 3062907HCID 3062907, compound

Product 1

HCID 13849380HCID 13849380, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In 6 ml of methylethylketone, 2.03 g of 6-methyl-4-phenyl-2-piperazinyl-thieno[2,3-d]pyrimidine, 1.25 g of 4-fluorophenacyl chloride and 0.73 g of triethylamine are reacted under reflux for 5 hours. After cooling, 70 ml of chloroform is added to the reaction mixture. The solution is washed twice with 100 ml of water and then saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After distilling off chloroform, crystallization from diethylether/methanol gives 2.68 g of the product which has a melting point of 141°-142° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter cooling
  3. washThe solution is washed twice with 100 ml of water
  4. dry with materialsaturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  5. distillationAfter distilling off
  6. customchloroform, crystallization from diethylether/methanol

Sources & evidence

ORD record
ord-3b2ba216faf0424d86d8dc22eda36a71
Source dataset
uspto-grants-1987_09
Patent number
US04695568

Reaction notes

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