(Diethylamino)sulfur trifluoride → HCID 59570990, compound

HRID 2192899Notes

Reaction equation

HRID 2192899 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13]O)[N:12]=1)([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:22])CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][F:22])[N:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 22280475(4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester

Product 1

HCID 59570990HCID 59570990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl[4-(hydroxymethyl)-1,3-thiazol-2-yl]carbamate (1.21 g) in dichloromethane (15 mL) was added diethylaminosulfur trifluoride (0.73 mL) under cooling in a dry ice-acetone bath, followed by stirring for 30 minutes under cooling as it is in a dry ice acetone bath. To the reaction mixture was added saturated aqueous sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated to obtain t-butyl[4-(fluoromethyl)-1,3-thiazol-2-yl]carbamate (480 mg) as a white solid.

Workup

  1. temperatureunder cooling in a dry ice-acetone bath
  2. temperatureunder cooling as it
  3. customis in a dry ice acetone bath
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f020f2c182b149ab8fa5da65dc3cb01e
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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