Water → HCID 86650036, compound

HRID 1892531Notes

Reaction equation

HRID 1892531 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:20]=[CH:19][C:7]([O:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>ClCCl.CN(C)C1C=CN=CC=1>[CH3:28][S:29]([O:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:19][CH:20]=1)(=[O:31])=[O:30]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86650037HCID 86650037, compound

Product 1

HCID 86650036HCID 86650036, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(4-{[4-(2-hydroxyethyl)phenoxy]methyl}-1,3-thiazol-2-yl)acetamide (310.0 mg, 1.060 mmol) in anhydrous dichloromethane (8 ml) were added triethylamine (0.27 ml, 1.91 mmol) and 4-dimethylaminopyridine (13.0 mg, 0.106 mmol), and the mixture was cooled to 0° C. Methanesulfonyl chloride (0.12 ml, 1.60 mmol) was added dropwise at 0° C. The mixture was warmed to room temperature and stirred for 1 hr. Iced water (20 ml) was added to the reaction mixture and the mixture was stirred for 20 min, extracted 3 times with ethyl acetate. The combined organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2-(4-{[2-(acetylamino)-1,3-thiazol-4-yl]methoxy}phenyl)ethyl methanesulfonate (410.8 mg, containing N-(4-{[4-(2-chloroethyl)phenoxy]methyl}-1,3-thiazol-2-yl)acetamide) as an orange solid.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringthe mixture was stirred for 20 min
  3. extractionextracted 3 times with ethyl acetate
  4. washThe combined organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7f8a3a4c8bb445cafed09ad6c78e71a
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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