Triethylamine → HCID 3113348, compound

HRID 2231837Notes

Reaction equation

HRID 2231837 reaction equation
Cl.[NH2:2][CH2:3][C:4]#[N:5].C(N(CC)CC)C.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14]>C(Cl)(Cl)Cl>[C:4]([CH2:3][NH:2][C:20](=[O:21])[C:19]1[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:24][CH:23]=1)#[N:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 3113348HCID 3113348, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 9.3 g (0.1 mole) aminoacetonitrile hydrochloride in 200 ml chloroform, 20.2 g (0.2 moles) triethylamine were added at once. After stirring one hour, 18.6 g (0.1 mole) p-nitrobenzoyl chloride were added in portions over about 15 minutes. The reaction mixture was stirred about 11/2 hours. Ice water, 100 ml, was added, resulting in separation of solids. The reaction mixture was allowed to stand in an ice bath for 30 minutes and then was filtered. The solids were air dried, washed with 200 ml water and then filtered to give yellow solids. The solids were dried in a vacuum oven at 50° C. until constant weight was attained, yielding 18.0 g of the above-identified product as a light yellow solid, melting point 147° C. to 149° C.

Workup

  1. additionwere added at once
  2. stirringThe reaction mixture was stirred about 11/2 hours
  3. customresulting in separation of solids
  4. waitto stand in an ice bath for 30 minutes
  5. filtrationwas filtered
  6. customdried
  7. washwashed with 200 ml water
  8. filtrationfiltered
  9. customto give yellow solids
  10. customThe solids were dried in a vacuum oven at 50° C. until constant weight

Sources & evidence

ORD record
ord-0f3a9649b43441ea8ba31db835932318
Source dataset
uspto-grants-1988_11
Patent number
US04785019

Reaction notes

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