Trifluoroacetic acid → Acetic acid, (4-(2-amino-4-thiazolyl)phenoxy)-

HRID 1107001Notes

Reaction equation

HRID 1107001 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:28]=[CH:27][C:17]([O:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[CH:16][CH:15]=2)[N:13]=1>C(Cl)Cl>[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:27][CH:28]=2)[N:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18790600HCID 18790600, compound

Product 1

HCID 3074898Acetic acid, (4-(2-amino-4-thiazolyl)phenoxy)-Yield 143.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (50 mL) was added to a solution of the product of example 2 (3.81 g, 12.4 mmol) in CH2Cl2 (50 mL). The resulting mixture was stirred at room temperature (20-22°) for 4 h, then concentrated under reduced pressure (coevaporated with CH2Cl2 and then Et2O). The residue was triturated with Et2O, then filtered and dried to afford 4.45 g (quantitative yield) of the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 7.67 (d, J=8.8 Hz, 2H), 6.97 (d, J=8.8 Hz, 2H), 6.96 (s, 1H), 4.72 (s, 2H). The product was used without further purification for the following reaction (example 4).

Workup

  1. concentrationconcentrated under reduced pressure (
  2. customThe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-f5c2784d7dfb4a33a2bacd05bdb70d81
Source dataset
uspto-grants-2000_05
Patent number
US06057451

Reaction notes

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