Methyl iodide → HCID 13073255, compound

HRID 67650Notes

Reaction equation

HRID 67650 reaction equation
[H-].[Na+].FC(F)(F)C1C=C(C2C(N)=C(C(OC)=O)SN=2)C=CC=1.CI.[CH3:25][NH:26][C:27]1[C:28]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:45])([F:44])[F:43])[CH:37]=2)=[N:29][S:30][C:31]=1[C:32]([O:34]C)=[O:33]>O1CCCC1>[F:45][C:42]([F:43])([F:44])[C:38]1[CH:37]=[C:36]([C:28]2[C:27]([NH:26][CH3:25])=[C:31]([C:32]([OH:34])=[O:33])[S:30][N:29]=2)[CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13073199Methyl 4-amino-3-[3-(trifluoromethyl)phenyl]-1,2-thiazole-5-carboxylateHCID 20265399HCID 20265399, compound

Product 1

HCID 13073255HCID 13073255, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.5 g. of sodium hydride (washed free of mineral oil) in 15 ml. of tetrahydrofuran was cooled to -20° C. and stirred. To the cold stirred suspension was added in one portion 3.0 g. of methyl 3-(3-trifluoromethylphenyl)-4-amino-5-isothiazolecarboxylate. The reaction mixture was warmed to room temperature, at which time 1.5 ml. of methyl iodide was added in one portion. The reaction mixture was stirred at ambient temperature for two hours, and then was added to 50 ml. of ice water. The aqueous mixture was extracted several times with diethyl ether. The ethereal extracts were combined, washed with water, dried and the solvent was removed by evaporation under reduced pressure to afford 2.0 g. of methyl 4-methylamino-3-(3-trifluoromethylphenyl)-5-isothiazolecarboxylate.

Workup

  1. additionA suspension of 0.5 g
  2. stirringTo the cold stirred suspension
  3. additionwas added in one portion 3.0 g
  4. stirringThe reaction mixture was stirred at ambient temperature for two hours
  5. additionwas added to 50 ml
  6. extractionThe aqueous mixture was extracted several times with diethyl ether
  7. washwashed with water
  8. customdried
  9. customthe solvent was removed by evaporation under reduced pressure
  10. customto afford 2.0 g

Sources & evidence

ORD record
ord-c0df6d52a0734ee18176b4e4379b42e5
Source dataset
uspto-grants-1982_08
Patent number
US04346094

Reaction notes

Loading…