Triethylamine → HCID 14349402, compound

HRID 2231845Notes

Reaction equation

HRID 2231845 reaction equation
Cl.[NH2:2][CH2:3][C:4]#[N:5].C(N(CC)CC)C.[C:13]1([C:23](Cl)=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl.C(Cl)Cl>[C:4]([CH2:3][NH:2][C:23]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)=[O:24])#[N:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 701461-Naphthalenecarbonyl chlorideHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 14349402HCID 14349402, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 9.3 g (0.1 mole) aminoacetonitrile hydrochloride and 20.2 g (0.2 moles) triethylamine in 200 ml chloroform which had been stirred for about 15 minutes to give a clear solution, the naphthoyl chloride from step (a) in 25 ml methylene chloride was dropped in over about 30 minutes in a slightly exothermic addition. The reaction mixture was stirred 20 minutes, and then was mixed with 200 ml ice water. A precipitate formed immediately; however, the mixture was cooled in an ice bath for about 15 minutes before being filtered. The precipitate was filtered, washed with 100 ml water and vacuum dried at about 55° C. to a constant weight, to give 18.7 g of the above-identified product as a beige solid, melting point 160° C. to 163° C.

Workup

  1. customto give a clear solution
  2. customA precipitate formed immediately
  3. temperaturehowever, the mixture was cooled in an ice bath for about 15 minutes
  4. filtrationbefore being filtered
  5. filtrationThe precipitate was filtered
  6. washwashed with 100 ml water and vacuum
  7. customdried at about 55° C. to a constant weight

Sources & evidence

ORD record
ord-5bc45661b9a4469f9fe93f24b0aa6f42
Source dataset
uspto-grants-1988_11
Patent number
US04785019

Reaction notes

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