Triethylamine → HCID 19418949, compound

HRID 864477Notes

Reaction equation

HRID 864477 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][C:10]1=[O:18].C(N(CC)CC)C>ClCCl>[S:2]([O:6][CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][C:10]1=[O:18])([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 335872-Benzoxazolinone, 3-(2-hydroxyethyl)-

Product 1

HCID 19418949HCID 19418949, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (2.21 ml, 3.265 g, 28.5 mmol) was added to a stirred solution of 3-(2-hydroxyethyl)benzoxazolin-2-one (5 g, 27.933 mmol) (J. Heterocyclic Chemistry 1988, 25, 1601) and triethylamine (5.947 ml, 4.318 g, 42.75 mmol) in dichloromethane (60 ml) and stirred for three days at room temperature. The solvent was evaporated in vacuo and the residue partitioned between water and ethyl acetate, washed with hydrochloric acid (2M, 5×50 ml), sodium hydrogen carbonate (2×20 ml), dried (MgSO4), filtered and the solvent removed in vacuo to give the title product.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between water and ethyl acetate
  3. washwashed with hydrochloric acid (2M, 5×50 ml), sodium hydrogen carbonate (2×20 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-31b1085223a94e2794833b40a2ee6c1f
Source dataset
uspto-grants-1996_10
Patent number
US05563147

Reaction notes

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