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

HRID 2064734Notes

Reaction equation

HRID 2064734 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].CN1CCOCC1.[CH3:13][O:14][C:15]([C:17]1[N:18]=[C:19]([CH3:29])[S:20][C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=1)=[O:16].O>C(Cl)Cl>[CH3:13][O:14][C:15]([C:17]1[N:18]=[C:19]([CH3:29])[S:20][C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][S:2]([CH3:1])(=[O:4])=[O:3])[CH:23]=1)=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 66844939HCID 66844939, compound

Product 1

HCID 669985805-(3-methanesulfonylamino-phenyl)-2-methyl-thiazole-4-carboxylic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (5.27 mmol) and 4-methylmorpholine (4.86 mmol) are added successively to a solution of 5-(3-amino-phenyl)-2-methyl-thiazole-4-carboxylic acid methyl ester (4.05 mmol) in DCM (50 mL). After stirring for 2 h water is added, the layers are separated and the aqueous layer is extracted once with DCM. The combined organic layers are washed with citric acid (10% solution in water), dried over MgSO4 and concentrated in vacuo to give a crude product which is used without further purification. LC-MS: tR=0.84 min; [M+H]+=327.2.

Workup

  1. additionis added
  2. customthe layers are separated
  3. extractionthe aqueous layer is extracted once with DCM
  4. washThe combined organic layers are washed with citric acid (10% solution in water)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3cf09d3d13474046922756bd5574745c
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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