Tetrahydrofuran → HCID 23025874, compound

HRID 1437481Notes

Reaction equation

HRID 1437481 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=3)[NH2:12])[O:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.O1CCCC1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>CN(C)C1C=CN=CC=1.O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([NH:12][S:31]([CH3:30])(=[O:33])=[O:32])[CH:13]=[CH:14][CH:15]=3)[O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23025926HCID 23025926, compound

Product 1

HCID 23025874HCID 23025874, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

To a solution of 3-(6-bromobenzoxazol-2-yl)aniline (Compound of Example 267) (925 mg), triethylamine (490 mg), 4-dimethylaminopyridine (39 mg) and tetrahydrofuran (35 ml) was added methanesulfonyl chloride (440 mg) at room temperature, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid, water, a saturated aqueous solution of sodium bicarbonate and water, successively, and dried over MgSO4. The solvent was distilled off under reduced pressure, and the resulting crystals were collected by filtration to obtain N-[3-(6-bromobenzoxazol-2-yl)phenyl]methane sulfonamide (686 mg, 58%). The crystals were recrystallized from ethyl acetate-hexane.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1 N hydrochloric acid, water
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and water, successively, and dried over MgSO4
  4. distillationThe solvent was distilled off under reduced pressure
  5. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-7cae387010b34ea1980be7a5d71d09e4
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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