Phosphorus oxychloride → N-(2-acetyl-5-methoxyphenyl)-2-thiazolecarboxamide

HRID 643853Notes

Reaction equation

HRID 643853 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].[NH2:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[C:17](=[O:19])[CH3:18].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:17]([C:10]1[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:9]=1[NH:8][C:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)=[O:7])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 27349031,3-Thiazole-2-carbaldehydeHCID 106786151-(2-Amino-4-methoxyphenyl)ethan-1-one

Product 1

HCID 57552136N-(2-acetyl-5-methoxyphenyl)-2-thiazolecarboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 2-thiazolecarboxaldehyde (500 mg, 3.87 mmol) in 35 mL of pyridine, 1-(2-amino-4-methoxyphenyl)ethanone (640 mg, 3.87 mmol) was added and the solution was cooled to −30° C. before POCl3 (750 μl, 8.13 mmol) was added drop wise. The reaction mixture was stirred at −10° C. for 1 hour and then at room temperature for 2 hours. The mixture was concentrated under vacuum and the residue was triturated with NaHCO3 to pH 7. The precipitate was filtrated, washed with water and dried. The amide was pure enough for the next step without purification (972 mg, 91%).

Workup

  1. additionwas added drop wise
  2. waitat room temperature for 2 hours
  3. concentrationThe mixture was concentrated under vacuum
  4. customthe residue was triturated with NaHCO3 to pH 7
  5. filtrationThe precipitate was filtrated
  6. washwashed with water
  7. customdried
  8. customThe amide was pure enough for the next step without purification (972 mg, 91%)

Sources & evidence

ORD record
ord-893cb057b2574c5e9b5158e8c9f78c15
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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