Water → HCID 21387176, compound

HRID 1834333Notes

Reaction equation

HRID 1834333 reaction equation
[C:1]1([S:7]([O-:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[CH:11]([N:14]=[N:15][C:16]1(Cl)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)([CH3:13])[CH3:12].O>CO>[CH:11]([N:14]=[N:15][C:16]1([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 2723840Benzenesulfinic acid, sodium saltHCID 21387085HCID 21387085, compound

Product 1

HCID 21387176HCID 21387176, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 6.57 grams (.04 moles) of sodium benzenesulfinate in 60 ml of 70% aqueous methanol in a 125 ml erlenmeyer flask was added 6.4 grams (.034 moles) of 1-isopropylazo-1-chlorocyclohexane (from Example 3-2) dropwise over 25 minutes while holding the temperature at 0° to 5° C with an ice bath. After the addition was complete, the reaction was stirred for 60 minutes at 0° to 5° C, poured into 200 ml cold water and extracted into 100 ml of pentane. The pentane solution was separated, washed with 50 ml of water, dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure on a rotating evaporator. The product was a yellow liquid and weighed 5.95 grams (59.5% crude yield). The infrared spectrum of the product was in agreement with the structure of 1-isopropylazo-1-(benzenesulfonyl)-cyclohexane.

Workup

  1. customat 0° to 5° C
  2. additionAfter the addition
  3. extractionextracted into 100 ml of pentane
  4. customThe pentane solution was separated
  5. washwashed with 50 ml of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe pentane evaporated under reduced pressure on a rotating evaporator

Sources & evidence

ORD record
ord-7203f1067e5e4cf0b9dbe460465356cf
Source dataset
uspto-grants-1978_01
Patent number
US04069377

Reaction notes

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