Hydrochloric Acid → HCID 15453204, compound

HRID 234326Notes

Reaction equation

HRID 234326 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([CH3:7])[C:3]=1[Br:8].[H-].[Na+].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].Cl>C1COCC1.O.CO>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:1][C:2]2[O:6][N:5]=[C:4]([CH3:7])[C:3]=2[Br:8])(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 104875194-Bromo-3-methylisoxazol-5-amine

Product 1

HCID 15453204HCID 15453204, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-amino-4-bromo-3-methylisoxazole (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol) in dry THF (1 ml) at 0°-5° C. After stirring at 0°-5° C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0° C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0°-5° C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170° C. (dec.).

Workup

  1. customthe reaction
  2. temperatureThe reaction mixture was re-cooled to 0° C.
  3. stirringStirring
  4. waitwas continued for 20 min. at 0°-5° C
  5. extractionextracted with dichloromethane
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2d102ee76d8342d39d2afbcc00065a74
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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