Triethylamine → HCID 13799783, compound

HRID 1906380Notes

Reaction equation

HRID 1906380 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C:10]1([C:15]#[N:16])[CH2:14][CH2:13][CH2:12][CH2:11]1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)(Cl)Cl>[C:15]([C:10]1([NH:9][S:18]([CH3:17])(=[O:20])=[O:19])[CH2:14][CH2:13][CH2:12][CH2:11]1)#[N:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 202117581-Aminocyclopentane-1-carbonitrile--hydrogen chloride (1/1)2×

Product 1

HCID 13799783HCID 13799783, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred mixture of 20.2 g (0.2 mole) triethylamine and 200 ml chloroform cooled in an ice bath, 14.7 g (0.1 mole) 1-amino-1-cyanocyclopentane hydrochloride (the product of Example 14) were spooned in over ten minutes to give a red solution. To that mixture, 11.5 g (0.1 mole) methanesulfonyl chloride in 25 ml chloroform were added dropwise over 30 minutes. The reaction mixture was stirred 30 minutes. The reaction mixture was washed with 25 ml concentrated hydrochloric acid which had been diluted to 50 ml with ice 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 13 g of the above-identified amber oily product.

Workup

  1. temperaturecooled in an ice bath
  2. customwere spooned in over ten minutes
  3. customto give a red solution
  4. washThe reaction mixture was washed with 25 ml concentrated hydrochloric acid which
  5. additionhad been diluted to 50 ml with ice water
  6. customseparated
  7. washThe organic layer was washed twice with 50 ml ice water
  8. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-f0a2e6e13bb14d1c85eb93993bc4e3bf
Source dataset
uspto-grants-1987_03
Patent number
US04652556

Reaction notes

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