Dimethylformamide → Ethyl 2-tritylaminothiazole-4-carboxylate

HRID 2107232Notes

Reaction equation

HRID 2107232 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCl.[NH2:24][C:25]1[S:26][CH:27]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:29]=1.CN(C)C=O>C(N(CC)CC)C>[C:7]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:29]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 6456Trityl chlorideHCID 73216Ethyl 2-aminothiazole-4-carboxylate

Product 1

HCID 15053536Ethyl 2-tritylaminothiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
-30 °C

Procedure

A mixture comprising 5 g of triphenylchloromethane and 15 ml of dichloromethane was added dropwise at -30° C. to a mixture comprising 3.1 g of ethyl 2-aminothiazole-4-carboxylate, 25 ml of dimethylformamide and 1.8 g of triethylamine. The reaction mixture was maintained at -30° C. for 10 minutes and was then stirred at room temperature for 2 hours. after which it was poured into ice water and extracted with ethyl acetate. The extract was washed successively with 0.1N hydrochloric acid and aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel chromatography, using as eluent a 10:1 by volume mixture of benzene and ethyl acetate. The crystals obtained thereby were washed with n-hexane, to afford the desired compound as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with 0.1N hydrochloric acid and aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated off under reduced pressure
  5. customthe residue was purified by silica gel chromatography
  6. additionby volume mixture of benzene and ethyl acetate
  7. customThe crystals obtained
  8. washthereby were washed with n-hexane

Sources & evidence

ORD record
ord-2b08955f6dea42c8988b651be9efa87f
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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