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

HRID 560260Notes

Reaction equation

HRID 560260 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH3:17])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)=[O:4].[CH3:18][CH2:19][O:20]C(C)=O.O>CN(C1C=CN=CC=1)C.C(OC(=O)C)(=O)C.CCOCC>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH3:17])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:19](=[O:20])[CH3:18])[CH:11]=1)=[O:4]

Participants

7

Reactant 3

HCID 962WaterHCID 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

TEA (14.2 mmol) and DMAP (4.05 mmol) are added successively to a solution of 5-(3-amino-phenyl)-2-methyl-thiazole-4-carboxylic acid methyl ester (4.05 mmol) in acetic anhydride (25 mL). After stirring for 30 min EtOAc and water are added, the layers are separated and the aq. layer is extracted once with EtOAc. The combined organic layers are washed with sat. aq. NH4Cl solution, sat. aq. NaHCO3 solution and water, dried over MgSO4 and concentrated in vacuo to give a crude product which is diluted with ether. The obtained suspension is filtered. The residue is washed with ether and dried in vacuo to give the desired product which is used without further purification. LC-MS: tR=0.81 min; [M+H]+=291.3.

Workup

  1. additionare added
  2. customthe layers are separated
  3. extractionthe aq. layer is extracted once with EtOAc
  4. washThe combined organic layers are washed with sat. aq. NH4Cl solution, sat. aq. NaHCO3 solution and water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a crude product which
  8. filtrationThe obtained suspension is filtered
  9. washThe residue is washed with ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-4c966a98e9a747b0a9746e47849302f0
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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