Toluene → HCID 54718074, compound

HRID 1657816Notes

Reaction equation

HRID 1657816 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6](=[O:14])(=[O:13])[CH2:5][CH2:4][CH:3]1[C:15]([O:17]C)=O.[NH2:19][C:20]1[CH:24]=[C:23]([CH3:25])[O:22][N:21]=1.C1(C)C=CC=CC=1>CCOCC>[OH:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6](=[O:13])(=[O:14])[CH2:5][CH2:4][C:3]=1[C:15]([NH:19][C:20]1[CH:24]=[C:23]([CH3:25])[O:22][N:21]=1)=[O:17]

Participants

5

Reactant 3

HCID 1140TolueneHCID 661723-Amino-5-methylisoxazoleHCID 21530394HCID 21530394, compound

Product 1

HCID 54718074HCID 54718074, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 17 g (0.05 mol) of crude methyl 2,3,4,5-tetrahydro-5-oxo-1-benzothiepin-4-carboxylate 1,1-dioxide, 6.0 g (0.061 mol) of 3-amino-5-methylisoxazole, and 350 ml of toluene was refluxed for 24 hours in a Soxhlet apparatus the thimble of which contained 20 g of Linde type 4A molecular sieve. The mixture was diluted with 500 ml of ether and the resulting precipitate (10 g) was collected and recrystallized from 400 ml of tetrahydrofuran to give 9.0 g of product mp 226°-228°. Recrystallization gave an analytical sample mp 227°-229°.

Workup

  1. temperaturewas refluxed for 24 hours in a Soxhlet apparatus the thimble of which
  2. customthe resulting precipitate (10 g) was collected
  3. customrecrystallized from 400 ml of tetrahydrofuran

Sources & evidence

ORD record
ord-dcd091349d814d71a5c472119a0d7f9a
Source dataset
uspto-grants-1976_06
Patent number
US03962261

Reaction notes

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