2-Amino-4-(4-chlorophenyl)thiazole → HCID 18475816, compound

HRID 2187400Notes

Reaction equation

HRID 2187400 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[F:14][C:15]([F:30])([F:29])[C:16]1[CH:17]=[C:18]([N:26]=[C:27]=[O:28])[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1>C(OCC)(=O)C>[F:14][C:15]([F:29])([F:30])[C:16]1[CH:17]=[C:18]([NH:26][C:27]([NH:1][C:2]2[S:3][CH:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=3)[N:6]=2)=[O:28])[CH:19]=[C:20]([C:22]([F:25])([F:23])[F:24])[CH:21]=1

Participants

4

Reactant 2

HCID 732412-Amino-4-(4-chlorophenyl)thiazoleHCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanate

Product 1

HCID 18475816HCID 18475816, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-amino-4-(4-chlorophenyl)thiazole (0.647 g, 3.07 mmol) in ethyl acetate (50 mL) was added 3,5-bis(trifluoromethyl)phenyl isocyanate (0.53 mL, 3.1 mmol). The mixture was refluxed for 16 hours, cooled to room temperature, and washed with 10% aqueous hydrochloric acid solution, water and brine. The mixture was dried (magnesium sulfate), filtered, and concentrated to provide a white solid. Flash chromatography over silica (hexanes/ethyl acetate) provided 0.850 g (59%) of the product as a white solid: 1H NMR (NMR (DMSO-d6) δ9.62 (br s, 1H), 8.18-8.17 (m, 2H), 7.92-7.88 (m, 2H), 7.72-7.66 (m, 2H), 7.49-7.46 (m, 2H) ppm.

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. washwashed with 10% aqueous hydrochloric acid solution, water and brine
  3. dry with materialThe mixture was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide a white solid

Sources & evidence

ORD record
ord-fc5f3c62cea144d9a8398d25c5117576
Source dataset
uspto-grants-2002_06
Patent number
US06410533B1

Reaction notes

Loading…