Ethanol → Ethyl 2-hydroxy-5-[[4-[(5-methyl-3-isoxazolyl)aminosulfonyl]phenyl]ethynyl]benzoate

HRID 743023Notes

Reaction equation

HRID 743023 reaction equation
[CH3:1][C:2]1[O:6][N:5](N)[CH2:4][CH:3]=1.C([O:11][C:12]1[CH:22]=[CH:21][C:20]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=O)C.[OH-].[K+].C(O)C.[N:40]1C=CC=CC=1>O.C(O)=O>[OH:11][C:12]1[CH:22]=[CH:21][C:20]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([NH:40][C:4]3[CH:3]=[C:2]([CH3:1])[O:6][N:5]=3)(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

8

Reactant 5

HCID 702EthanolHCID 1049PyridineHCID 14797Potassium HydroxideHCID 19423378HCID 19423378, compoundHCID 194234192-Amino-5-methylisoxazole

Product 1

HCID 19423380Ethyl 2-hydroxy-5-[[4-[(5-methyl-3-isoxazolyl)aminosulfonyl]phenyl]ethynyl]benzoate

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

5-methyl-2-isoxazolamine (1.2 g, 12 mmol) was dissolved in dry pyridine (20 ml) and ethyl 2-acetyloxy-5-[(4-chlorosulfonylphenyl)ethynyl]-benzoate (4.1 g, 10 mmol) was added. The solution was kept at ambient temperature for 72 h. The solvent was evaporated and the residue dissolved in a small amount of tetrahydrofuran. The solution was added to a refluxing solution of potassium hydroxide (2.5 g, 38 mmol) in water (100 ml). After 5 min, ethanol (50 ml) was added and the solution acidified with formic acid to produce a precipitate. The solid was collected by filtration, washed with water and dried. It was recrystallize three times from ethanol. Yield 1.5 g, 35%.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in a small amount of tetrahydrofuran
  3. waitAfter 5 min
  4. customto produce a precipitate
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. customdried
  8. customIt was recrystallize three times from ethanol

Sources & evidence

ORD record
ord-65196552c32a428abad6512e31025c6c
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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