Diethyl Ether → 3-Ethyl-5-hexylsulfonamido-2-methylbenzoxazolium p-toluenesulfonate

HRID 1199329

Reaction equation

HRID 1199329 reaction equation
[CH2:1]([S:7]([NH:10][C:11]1[CH:12]=[CH:13][C:14]2[O:18][C:17]([CH3:19])=[N:16][C:15]=2[CH:20]=1)(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:21]1([CH3:33])[CH:26]=[CH:25][C:24]([S:27]([O:30]CC)(=[O:29])=[O:28])=[CH:23][CH:22]=1.[CH2:34](OCC)[CH3:35]>CO>[C:21]1([CH3:33])[CH:22]=[CH:23][C:24]([S:27]([O-:30])(=[O:28])=[O:29])=[CH:25][CH:26]=1.[CH2:34]([N+:16]1[C:15]2[CH:20]=[C:11]([NH:10][S:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])(=[O:9])=[O:8])[CH:12]=[CH:13][C:14]=2[O:18][C:17]=1[CH3:19])[CH3:35]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6638Ethyl p-methylbenzenesulfonateHCID 150510645-Hexylsulfonamido-2-methylbenzoxazole

Product 1

HCID 199934523-Ethyl-5-hexylsulfonamido-2-methylbenzoxazolium p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 60 g of intermediate A and 44 g ethyl p-toluenesulfonate was heated in a round bottom flask at 150° C. for 5 minutes. Upon cooling to room temperature, the crude brown mass was almost solidified. The product was dissolved in 25 ml methanol and poured into 300 ml diethyl ether with rapid stirring for 1 hour. The solid precipitate was chilled at 2° C. overnight, and then filtered. The tan powder was thoroughly washed with ether and recrystallized from 200 ml hot isopropyl alcohol to yield 23.4 g of 3-ethyl-5-hexylsulfonamido-2-methylbenzoxazolium p-toluenesulfonate (Intermediate B).

Workup

  1. temperatureUpon cooling to room temperature
  2. temperatureThe solid precipitate was chilled at 2° C. overnight
  3. filtrationfiltered
  4. washThe tan powder was thoroughly washed with ether
  5. customrecrystallized from 200 ml hot isopropyl alcohol

Sources & evidence

ORD record
ord-a0e387c961e1424b9d7c666584ccb238
Source dataset
uspto-grants-1990_02
Patent number
US04900653

Linked notes

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