Hydrochloric Acid → HCID 15453204, compound

HRID 1738415Notes

Reaction equation

HRID 1738415 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×

Conditions

Temperature
2.5 °C

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. temperaturethe reaction was warmed to room temperature for 10 min.
  2. customthe reaction
  3. temperatureThe reaction mixture was re-cooled to 0° C.
  4. stirringStirring
  5. waitwas continued for 20 min. at 0-5° C
  6. extractionextracted with dichloromethane
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-158bcc2cc33149ce87391a9fbbd5587b
Source dataset
uspto-grants-1999_10
Patent number
US05962490

Reaction notes

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