Water → HCID 54103281, compound

HRID 981450Notes

Reaction equation

HRID 981450 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C.[NH:15]([CH2:19][CH2:20][OH:21])[CH2:16][CH2:17][OH:18].[OH-].[Na+].O>ClCCl>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:15]([CH2:19][CH2:20][OH:21])[CH2:16][CH2:17][OH:18])(=[O:12])=[O:13])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8113DiethanolamineHCID 14798Sodium HydroxideHCID 129257104-(Chlorosulfonyl)phenyl acetate

Product 1

HCID 54103281HCID 54103281, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 46.9 g (0.20 mole) of 4-acetoxybenzenesulfonyl chloride (I) in 400 ml dichloromethane contained in a 500-ml round-buttomed flask was dried over magnesium sulfate, then filtered and placed in a 3-liter, 3-necked, round-buttomed flask equipped with a stirrer, an additional funnel, a condenser and a thermometer. After subsequent cooling to 5° C., 142.2 g (0.70 mole) of diethanolamine (II) were added slowly with stirring. The reaction mixture was allowed to reach room temperature and was then stirred for 2 hours, followed by the addition of a mixture of 30 ml sodium hydroxide (50%) and 20 ml water. The resulting two phase mixture was stirred at room temperature for an additional two hours. The aqueous layer was extracted with two 150-ml portions of dichloromethane, and the aqueous phase was cooled in an ice bath and acidified with concentrated HCl to a pH of 2.0. Sodium hydroxide was added to saturate the aqueous phase, which was then extracted with ten 300-ml portions of ethylacetate, followed by roto-evaporation of the combined ethyl acetate extracts to dryness. A white solid (III) was collected, washed with heptane and dried under vacuum. The yield was 24.7 g (42.3%).

Workup

  1. dry with materialwas dried over magnesium sulfate
  2. filtrationfiltered
  3. custom3-necked, round-buttomed flask equipped with a stirrer, an additional funnel, a condenser
  4. customto reach room temperature
  5. stirringwas then stirred for 2 hours
  6. stirringThe resulting two phase mixture was stirred at room temperature for an additional two hours
  7. extractionThe aqueous layer was extracted with two 150-ml portions of dichloromethane
  8. temperaturethe aqueous phase was cooled in an ice bath
  9. additionSodium hydroxide was added
  10. concentrationto saturate the aqueous phase, which
  11. extractionwas then extracted with ten 300-ml portions of ethylacetate
  12. customfollowed by roto-evaporation of the combined ethyl acetate
  13. customA white solid (III) was collected
  14. washwashed with heptane
  15. customdried under vacuum

Sources & evidence

ORD record
ord-b6dbd6b0f37248ef821a25fd8712cd6b
Source dataset
uspto-grants-1991_02
Patent number
US04992359

Reaction notes

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