Methanesulfonyl chloride → HCID 86681669, compound

HRID 571257Notes

Reaction equation

HRID 571257 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>N1C=CC=CC=1>[CH3:17][S:18]([NH:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 6504213HCID 6504213, compound

Product 1

HCID 86681669HCID 86681669, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl 2-(6-amino-2-oxobenzo[d]oxazol-3(2H)-yl)acetate (0.497 g, 2.237 mmol) in pyridine (15 ml) was cooled to 0° C., and methanesulfonyl chloride (0.209 ml, 2.68 mmol) was added. The mixture was warmed to room temperature and stirred for 1 hour. The solvent was removed and the residue was portioned between ethyl acetate and 1N HCl. The organic phase was washed with brine and dried over sodium sulfate; the solvent was removed and the crude was purified by trituration with diethyl ether affording methyl 2-(6-(methylsulfonamido)-2-oxobenzo[d]oxazol-3(2H)-yl)acetate (0.523 g, 1.742 mmol, 78% yield). MS/ESI+ 300.9 [MH]+.

Workup

  1. customThe solvent was removed
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed
  5. customthe crude was purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-587c1733e89045a2979015e264068860
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

Loading…