p-Toluenesulfonic acid → HCID 19899075, compound

HRID 1196662Notes

Reaction equation

HRID 1196662 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O-:10])=[O:9])[CH2:3]1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[C:17]1(C)C=CC(S(O)(=O)=O)=C[CH:18]=1.C(N(CC)CC)C.[Cl:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1>C1(C)C=CC=CC=1>[Cl:35][C:36]1[CH:44]=[CH:43][C:39]([C:40]([CH:5]2[CH2:6][CH:7]=[CH:2][CH2:3][C:4]2([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]([O:10][CH2:17][CH3:18])=[O:9])=[O:41])=[CH:38][CH:37]=1

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 19899084HCID 19899084, compound

Product 1

HCID 19899075HCID 19899075, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 3.12 g (0.02 mol) of 3-oxocyclohexanecarboxylate, 1.91 g (0.022 mol) of morpholine and 0.01 g of p-toluenesulfonic acid in 300 ml of toluene was heated under reflux for 6 hours in a Dean-Stark apparatus. The solution was cooled to 0° C. and there were added 2.02 g (0.02 mol) of triethylamine in 5 ml of toluene followed by 3.83 g (0.02 mol) of p-chlorobenzoyl chloride in 30 ml of toluene over a period of 0.5 hour. The mixture was stirred at 20° C. for 3 hours and then heated at 60° C. for 3 hours. The solution was cooled and filtered. The filtrate was evaporated to give ethyl 2-(4-chlorobenzoyl)-1-morpholino-4-cyclohexenecarboxylate as a gum which was dissolved in 10 ml of ethanol and 5 ml of pyridine and treated with 1.4 g (0.02 mol) of hydroxylamine hydrochloride. The mixture was then heated under reflux for 2 hours. The solvents were removed by evaporation, 2N hydrochloric acid was added to the residue and the product was extracted with diethyl ether. Evaporation of the ethereal extract gave 1 g of methyl 3-(4-chlorophenyl)-4,5,6,7-tetrahydro-2,1-benzisoxazole-6-carboxylate of melting point 141°-143° C. (from ethyl acetate/hexane).

Workup

  1. temperatureunder reflux for 6 hours in a Dean-Stark apparatus
  2. temperatureheated at 60° C. for 3 hours
  3. temperatureThe solution was cooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-5f3a0412159646b3a9627eb862b01ff8
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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