Triethylamine → HCID 3343154, compound

HRID 1447983Notes

Reaction equation

HRID 1447983 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH2:10][C:11]#[N:12].[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18](Cl)=[O:19]>C(Cl)(Cl)Cl.ClCCl>[C:11]([CH2:10][NH:9][C:18]([C:14]1[O:13][CH:17]=[CH:16][CH:15]=1)=[O:19])#[N:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 3343154HCID 3343154, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A 20.2-g (0.2 mol) sample of triethylamine was added dropwise over 20 minutes to a stirred and cooled (ice bath) mixture of 9.3 g (0.1 mol) aminoacetonitrile hydrochloride in 150 ml chloroform. A solution of 13.2 g (0.1 mol) 2-furoyl chloride in 25 ml dichloromethane was then added dropwise over 20 minutes. The ice bath was removed and the reaction mixture stirred for 25 minutes. The reaction mixture was then washed with water, dried over magnesium sulfate and evaporated to give 7.4 g of crude N-cyanomethyl-2-furamide, as a beige solid, m.p. 85°-93° C. Recrystallization from benzene gave the furamide as a white solid, m.p. 101°-102° C. Elemental analysis for C7H6N2O showed: %C, calc. 56.0, found 56.0; %H, calc. 4.06, found 4.11; %N, calc. 18.7, found 19.1.

Workup

  1. temperaturecooled
  2. customThe ice bath was removed
  3. stirringthe reaction mixture stirred for 25 minutes
  4. washThe reaction mixture was then washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-d11b59c6d1124b568a5ad86dfe8389f5
Source dataset
uspto-grants-1979_12
Patent number
US04179441

Reaction notes

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