Water → 5-(3-acetylamino-phenyl)-2-methyl-thiazole-4-carboxylic Acid Methyl Ester

HRID 2064479Notes

Reaction equation

HRID 2064479 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]([C:12]1[N:13]=[C:14]([CH3:24])[S:15][C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=1)=[O:11].[CH3:25][CH2:26][O:27]C(C)=O.O>CN(C1C=CN=CC=1)C.C(OC(=O)C)(=O)C.CCOCC>[CH3:8][O:9][C:10]([C:12]1[N:13]=[C:14]([CH3:24])[S:15][C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:26](=[O:27])[CH3:25])[CH:18]=1)=[O:11]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66844939HCID 66844939, compound

Product 1

HCID 668444965-(3-acetylamino-phenyl)-2-methyl-thiazole-4-carboxylic Acid Methyl Ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Triethylamine (14.2 mmol) and DMAP (4.00 mmol) are added to a solution of 5-(3-Amino-phenyl)-2-methyl-thiazole-4-carboxylic acid methyl ester (4.00 mmol) in acetic acid anhydride (25 mL). After 30 min EtOAc and water are added, the layers are separated and the aqueous layer is extracted once with EtOAc. The combined organic layers are washed twice with sat aqueous ammonium chloride solution, once with sat aqueous NaHCO3 solution and once with water and the solvents are removed in vacuo. The residue is diluted with EtOAc and extracted three times with sat aqueous NaHCO3 solution. The organic layer is dried over MgSO4 and concentrated in vacuo to give a crude solid which is diluted with ether. The obtained suspension is filtered and the residue is washed with ether to give the desired acetamide. LC-MS: tR=0.81 min; [M+H]+=291.3.

Workup

  1. customthe layers are separated
  2. extractionthe aqueous layer is extracted once with EtOAc
  3. washThe combined organic layers are washed twice with sat aqueous ammonium chloride solution
  4. customonce with water and the solvents are removed in vacuo
  5. additionThe residue is diluted with EtOAc
  6. extractionextracted three times with sat aqueous NaHCO3 solution
  7. dry with materialThe organic layer is dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto give a crude solid which
  10. filtrationThe obtained suspension is filtered
  11. washthe residue is washed with ether

Sources & evidence

ORD record
ord-61c3a0ed592f44f6ad0478ac80eef5d6
Source dataset
uspto-grants-2012_10
Patent number
US08288429B2

Reaction notes

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