Water → HCID 22311651, compound

HRID 965600Notes

Reaction equation

HRID 965600 reaction equation
Cl[C:2]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:5]([C:6]([O:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:7])=[CH:4][C:3]=1[N+:22]([O-:24])=[O:23].[S:25]([O-:28])([O-:27])=[O:26].[Na+:29].[Na+].O.C(O)(C)C>C(#N)C>[CH:11]1([CH2:10][CH2:9][O:8][C:6]([C:5]2[CH:17]=[C:18]([N+:19]([O-:21])=[O:20])[C:2]([S:25]([O-:28])(=[O:27])=[O:26])=[C:3]([N+:22]([O-:24])=[O:23])[CH:4]=2)=[O:7])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[Na+:29]

Participants

6

Reactant 4

HCID 962Water2×HCID 3776IsopropanolHCID 24437Sodium SulfiteHCID 22311653HCID 22311653, compound2×

Product 1

HCID 22311651HCID 22311651, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
80 °C

Procedure

50 parts of 2-cyclohexylethyl 4-chloro-3,5-dinitrobenzoate was dissolved in 157 parts of acetonitrile. To the solution was added dropwise the solution of 35.4 parts of sodium sulfite and 72 parts of water at room temperature. To the mixed solution 1965 parts of acetonitrile little by little, and then was added 500 parts of water to obtain uniform solution. The solution was heated to 80° C. and maintained the temperature with stirring for 3 hours. After checking the disapearance of 2-cyclohexylethyl 4-chloro-3,5-dinitrobenzoate by HPLC, the resulting solution was concentrated 80° C. under reduced pressure. To the concentrate was added 80 parts of methanol, and stirred for 30 minutes. The crystals precipitated were filtrated and washed with 40 parts of methanol, and the filtrate was concentrated at 80° C. to obtain yellow crystals. Further, to the crystals was added 400 ml of isopropanol and the mixture was subjected to azeotropic dehydration. The crystals were filtrated and washed with 200 ml of isopropanol, and dried to obtain 42.2 parts of sodium 4-(2-cyclohexylethoxycarbonyl)-2,6-dinitrobenzenesulfonate (Yield:90.7%, Yield:70%).

Workup

  1. customto obtain uniform solution
  2. temperaturemaintained the temperature
  3. concentrationthe resulting solution was concentrated 80° C. under reduced pressure
  4. additionTo the concentrate was added 80 parts of methanol
  5. stirringstirred for 30 minutes
  6. customThe crystals precipitated
  7. filtrationwere filtrated
  8. washwashed with 40 parts of methanol
  9. concentrationthe filtrate was concentrated at 80° C.
  10. customto obtain yellow crystals
  11. filtrationThe crystals were filtrated
  12. washwashed with 200 ml of isopropanol
  13. customdried

Sources & evidence

ORD record
ord-7f88f0659ab44580b8af5860fff51d66
Source dataset
uspto-grants-2005_10
Patent number
US06951706B2

Reaction notes

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