1-Butanesulfonyl chloride → HCID 13799776, compound

HRID 1906381Notes

Reaction equation

HRID 1906381 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[C:3]#[N:4].[CH2:7]([S:11](Cl)(=[O:13])=[O:12])[CH2:8][CH2:9][CH3:10]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH3:5][C:2]([NH:1][S:11]([CH2:7][CH2:8][CH2:9][CH3:10])(=[O:13])=[O:12])([CH3:6])[C:3]#[N:4]

Participants

5

Reactant 2

HCID 754301-Butanesulfonyl chlorideHCID 880222-Amino-2-methylpropionitrile

Product 1

HCID 13799776HCID 13799776, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent2×

Procedure

To a stirred mixture of 8.4 g (0.1 mole) 2-amino-2-methyl-propionitrile and 12.2 g (0.1 mole) 4-dimethylaminopyridine in 125 ml chloroform, 15.7 g (0.1 mole) 1-butanesulfonyl chloride in 25 ml chloroform were added dropwise over 20 minutes, with evolution of heat and separation of solids. The reaction mixture was refluxed 2.5 hours. After cooling to room temperature, the reaction mixture was washed with 25 ml concentrated hydrochloric acid which had been diluted with 25 ml water. The layers were phase separated. The organic layer was washed twice with 50 ml ice water, dried over magnesium sulfate and stripped to give 8.0 g of the above-identified product, as a dark red oil.

Workup

  1. additionwere added dropwise over 20 minutes, with evolution
  2. temperatureof heat
  3. customseparation of solids
  4. temperatureThe reaction mixture was refluxed 2.5 hours
  5. washthe reaction mixture was washed with 25 ml concentrated hydrochloric acid which
  6. additionhad been diluted with 25 ml water
  7. customseparated
  8. washThe organic layer was washed twice with 50 ml ice water
  9. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-654fb19d164b431781410ff9b9c2deb5
Source dataset
uspto-grants-1987_03
Patent number
US04652556

Reaction notes

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