Water → HCID 178449071, compound

HRID 2210993Notes

Reaction equation

HRID 2210993 reaction equation
[S:1](Cl)(Cl)(=[O:3])=[O:2].C(N(CC)CC)C.[CH2:13]([NH:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].O>C(Cl)(Cl)Cl>[CH2:13]([N:17]([CH2:18][CH2:19][CH2:20][CH3:21])[SH:1](=[O:3])=[O:2])[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8148DibutylamineHCID 8471TriethylamineHCID 24648Sulfuryl chloride

Product 1

HCID 178449071HCID 178449071, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 160.6 ml sulfuryl chloride in 1000 ml chloroform in a round bottomed flask equipped with a dropping funnel, thermometer, and magnetic stirrer was added dropwise 139.4 ml triethylamine and 168.5 ml dibutylamine with cooling in an ice-water bath to maintain a temperature of 15°-20° C. After the addition was complete, the reaction mixture was stirred without cooling for an additional hour, then poured into a mixture of ice and water (2000 ml). The chloroform phase was separated and washed with 10% hydrochloric acid (1000 ml) followed by ice cold water. The solution was dried over anhydrous calcium chloride (4-20 mesh). Evaporation of the solvent gave 147.7 g N,N-dibutylsulfonamide as a colorless oil.

Workup

  1. temperaturewith cooling in an ice-water bath
  2. temperatureto maintain a temperature of 15°-20° C
  3. additionAfter the addition
  4. temperaturewithout cooling for an additional hour
  5. customThe chloroform phase was separated
  6. washwashed with 10% hydrochloric acid (1000 ml)
  7. dry with materialThe solution was dried over anhydrous calcium chloride (4-20 mesh)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4f52ce7098e3407ebf9bcd0f50ba2399
Source dataset
uspto-grants-1995_10
Patent number
US05461155

Reaction notes

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