Diethyl Ether → Methyl 5-phenyl-2-{[3-(trifluoromethyl)phenyl]amino}4-thiazolecarboxylate

HRID 359260Notes

Reaction equation

HRID 359260 reaction equation
[C:1]1([C:7]2[S:11][C:10](Cl)=[N:9][C:8]=2[C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:17][C:18]1[CH:19]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:22][CH:23]=1.C(OCC)C>O>[C:1]1([C:7]2[S:11][C:10]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=3)=[N:9][C:8]=2[C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 73753-(Trifluoromethyl)anilineHCID 12821997Methyl 2-chloro-5-phenyl-4-thiazolecarboxylate

Product 1

HCID 20064764Methyl 5-phenyl-2-{[3-(trifluoromethyl)phenyl]amino}4-thiazolecarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction vessel was charged with 2.8 g of methyl 5-phenyl-2-chloro-4-thiazolecarboxylate and 9.7 g of meta-aminobenzotrifluoride. The reaction mixture was stirred overnight and then heated and stirred at 150° C. for about 6 hours during which time a crystalline solid appeared. The mixture was treated with ethyl ether and water. The ether extract was dried with magnesium sulfate and concentrated. The residue was crystallized from anhydrous ethyl ether to provide a white amorphous powder (m.p. 147°-149° C.) identified in Table I.

Workup

  1. temperatureheated
  2. stirringstirred at 150° C. for about 6 hours during which time a crystalline solid
  3. extractionThe ether extract
  4. dry with materialwas dried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was crystallized from anhydrous ethyl ether

Sources & evidence

ORD record
ord-8955d1581eff4c428c6e2f5fe2a66864
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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