Triethylamine → HCID 22890470, compound

HRID 993136Notes

Reaction equation

HRID 993136 reaction equation
[NH2:1][CH2:2][C:3]#[N:4].C(N(CC)CC)C.[CH2:12]([S:15](Cl)(=[O:17])=[O:16])[CH2:13][CH3:14]>ClCCCl>[C:3]([CH2:2][NH:1][S:15]([CH2:12][CH2:13][CH3:14])(=[O:17])=[O:16])#[N:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10901AminoacetonitrileHCID 662791-Propanesulfonyl chloride

Product 1

HCID 22890470HCID 22890470, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Aminoacetonitrile (14.25 g, 92.5 mmoles) was dissolved in 1,2-dichloroethane (150 ml) and the reaction was placed under N2. Triethylamine (32.76 g, 324 mmoles) was added and the reaction was cooled to zero degrees Celsius. A solution of propane-1-sulfonyl chloride (13.19 g, 92.5 mmoles) in 1,2-dichloroethane (20 ml) was added dropwise and the reaction was allowed to warm to room temperature and was stirred for 16 hours. Thin-layer chromatography showed the presence of a new product with a higher Rf. The solvent was removed in vacuo and the crude product was submitted to flash chromatography (methylene chloride:ethyl acetate, 9:1) to yield 10.56 g of propane-1-sulfonic acid cyanomethyl-amide. 1HNMR (CDCl3): 5.40 (s, 1H), 4.11 (s, 2H), 3.15 (m, 2H), 1.89 (q, 2H), 1.10 (t, 3H).

Workup

  1. temperaturethe reaction was cooled to zero degrees Celsius
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a6e9638e12b2478db6bd73f14d8d0ac0
Source dataset
uspto-grants-2002_10
Patent number
US06472393B1

Reaction notes

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