Toluene → N-(1-Methylethyl)-N-(2-hydroxyethyl)-1,2-benzisoxazole-3-carboxamide

HRID 483440Notes

Reaction equation

HRID 483440 reaction equation
C(O[C:4]([C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][N:7]=1)=[O:5])C.[CH3:15][CH:16]([NH:18][CH2:19][CH2:20][OH:21])[CH3:17].C1(C)C=CC=CC=1>CCOCC>[CH3:15][CH:16]([N:18]([CH2:19][CH2:20][OH:21])[C:4]([C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:17]

Participants

5

Reactant 3

HCID 1140TolueneHCID 79942-(Isopropylamino)ethanolHCID 14177940Ethyl 1,2-benzoxazole-3-carboxylate

Product 1

HCID 10332255N-(1-Methylethyl)-N-(2-hydroxyethyl)-1,2-benzisoxazole-3-carboxamideYield 81.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of ethyl-1,2-benzisoxazole-3-carboxylate (10.0 g), 2-(1-methylethylamino)ethanol (16.1 g) and toluene (80 ml) was heated to 140° C. in a bomb for 4 hrs. The solution was diluted with ether (50 ml), washed with 5% sodium bicarbonate solution, water, brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with 60% ethyl acetate in hexanes to give 10.6 g (81.4%) of product. Recrystallization from dichloromethane/hexanes afforded the analytical sample, mp 92°-94° C.

Workup

  1. washwashed with 5% sodium bicarbonate solution, water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed on silica gel
  5. washeluting with 60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4b94fa192a524711b2433c5f3a14edc1
Source dataset
uspto-grants-1993_07
Patent number
US05225412

Reaction notes

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