Sulfuric Acid → 4-isopropyl-6-[3-(carboxy)propoxy]-2-[1-(4-chlorophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289876Notes

Reaction equation

HRID 1289876 reaction equation
[CH:1]([C:4]1[C:9]2[C:10](=[O:33])[N:11]([CH2:15][O:16][C:17]3[N:21]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)[N:20]=[C:19]([C:29]([F:32])([F:31])[F:30])[CH:18]=3)[S:12](=[O:14])(=[O:13])[C:8]=2[CH:7]=[C:6]([O:34][CH2:35][CH2:36][CH2:37][C:38]([O:40]CC2C=CC=CC=2)=[O:39])[CH:5]=1)([CH3:3])[CH3:2].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH:1]([C:4]1[C:9]2[C:10](=[O:33])[N:11]([CH2:15][O:16][C:17]3[N:21]([C:22]4[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=4)[N:20]=[C:19]([C:29]([F:32])([F:31])[F:30])[CH:18]=3)[S:12](=[O:14])(=[O:13])[C:8]=2[CH:7]=[C:6]([O:34][CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])[CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 189225544-isopropyl-6-[3-(phenylmethyloxycarbonyl)propoxy]-2-[1-(4-chlorophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 189225424-isopropyl-6-[3-(carboxy)propoxy]-2-[1-(4-chlorophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxideYield 70.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-isopropyl-6-[3-(phenylmethyloxycarbonyl)propoxy]-2-[1-(4-chlorophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (4.19 g; 6.055 mmol) and 50 ml of 20% sulfuric acid in 80 ml of dioxane was heated at 100° C. for 20 hours. The mixture was cooled, poured into ice, neutralized with sodium bicarbonate solution (160 ml, to pH=5), and the resulting solid was filtered and recrystallized (3×, ethyl acetate/hexane; methylene chloride/hexane; and acetonitrile) to afford 2.56 g of 4-isopropyl-6-[3-(carboxy)propoxy]-2-[1-(4-chlorophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =4-Cl--Ph; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-O(CH2)3CO2H) as a white solid, 162°-164° C.

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured into ice
  3. filtrationthe resulting solid was filtered
  4. customrecrystallized (3×, ethyl acetate/hexane; methylene chloride/hexane; and acetonitrile)

Sources & evidence

ORD record
ord-517fb03f43ec46b5af61e31e080e6736
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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