Triethylamine → HCID 14473354, compound

HRID 1607380Notes

Reaction equation

HRID 1607380 reaction equation
Cl[CH2:2][CH2:3][S:4](Cl)(=[O:6])=[O:5].[CH2:8]([O:10][CH:11](OCC)[CH:12](N)[CH2:13][CH3:14])[CH3:9].C([N:21](CC)CC)C>C(Cl)Cl>[CH:3]([S:4]([N:21]1[CH2:14][CH2:13][CH2:12][CH:11]1[O:10][CH2:8][CH3:9])(=[O:6])=[O:5])=[CH2:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 22145180HCID 22145180, compound

Product 1

HCID 14473354HCID 14473354, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a vigorously stirred mixture of 25.7 g (0.158 mol) of 2-chloroethanesulfonyl chloride in 100 mL of CH2Cl2 was slowly added a mixture of 25.4 g (0.158 mol) of aminobutyraldehyde diethyl acetal, 35 g (0.34 mol) of triethylamine and 50 mL of CH2Cl2. The temperature was maintained below 10° C. Stirring was continued for 2 h. The solution was filtered to remove solid Et3NHCl and extracted with 10 mL of 10% HCl (pH 3.0), then 10 mL of 4% NaHCO3. The organic layer was dried with MgSO4 and concentrated on a rotary evaporator to yield 25.7 g of brown liquid containing one major and one significant minor component by gc (~78% at 10.83 min, 8% at 9.12 min). Distillation of an aliquot on a kugelrohr apparatus (130° C., 0.5 torr) increased the ratio of the short retention time peak.

Workup

  1. additionwas slowly added
  2. temperatureThe temperature was maintained below 10° C
  3. filtrationThe solution was filtered
  4. customto remove solid Et3NHCl
  5. extractionextracted with 10 mL of 10% HCl (pH 3.0)
  6. dry with materialThe organic layer was dried with MgSO4
  7. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-92dbb51ce3f540be82c18b2570130c28
Source dataset
uspto-grants-1989_09
Patent number
US04864055

Reaction notes

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