Hydrochloric Acid → HCID 22735975, compound

HRID 51002Notes

Reaction equation

HRID 51002 reaction equation
[F:1][C:2]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][OH:9])=[O:5].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].Cl>C(Cl)Cl.C(OCC)(=O)C>[CH3:22][S:23]([O:9][CH2:8][CH2:7][NH:6][C:4](=[O:5])[C:3]1[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:2]=1[F:1])(=[O:25])=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 176835502,4-difluoro-N-(2-hydroxyethyl)benzamide

Product 1

HCID 22735975HCID 22735975, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,4-difluoro-N-(2-hydroxyethyl)benzamide (299 mg, 1.49 mmol) and triethylamine (302 mg, 2.98 mmol) in CH2Cl2 under nitrogen at 0° C. was added methanesulfonyl chloride (335 mg, 2.98 mmol) The reaction mixture was stirred for 1 h at 0° C. 1 N HCl (5 mL) was added to quench the reaction and the solution was diluted with ethyl acetate (100 mL), washed with saturated NaHCO3 (100 mL) and saturated NaCl (100 mL), dried over MgSO4, filtered and concentrated in vacuo. Purification by column chromatography (hexanes:EtOAc 4:1) yielded 2-[(2,4-difluorobenzoyl)amino]ethyl methanesulfonate (300 mg, 72%) as a clear liquid.

Workup

  1. customto quench
  2. customthe reaction
  3. washwashed with saturated NaHCO3 (100 mL) and saturated NaCl (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (hexanes:EtOAc 4:1)

Sources & evidence

ORD record
ord-be54c9d54d2047e7bdb3f988f7424946
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

Loading…