Triethylamine → HCID 4373767, compound

HRID 1579920Notes

Reaction equation

HRID 1579920 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6](Cl)=[O:7].C(N(CC)CC)C.Cl.[NH2:22][CH2:23][C:24]#[N:25]>C1C=CC=CC=1>[C:23]([CH2:24][NH:25][C:6](=[O:7])[CH2:5][O:4][C:3]1[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:2]=1[Cl:1])#[N:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69887(2,4-Dichlorophenoxy)acetyl chlorideHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 4373767HCID 4373767, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 11.95 g. (0.05 mole) of 2,4 dichlorophenoxyacetyl chloride in 50 ml. of benzene was added slowly to a stirred mixture of 10.1 g. (0.10 mole) of triethylamine and 4.2 g. (0.05 mole) aminoacetonitrile hydrochloride in 200 ml. of benzene. The mixture was stirred for 2 hours at room temperature and then washed successively with water, 5% sodium hydroxide solution, water, 5% hydrochloric acid solution, and water and then dried over magnesium sulfate. The resultant filtrate was concentrated under vacuum to give a solid which was crystallized from dilute ethanol to give 8.6 g. (66% yield) of product having a melting point of 107°-108° C.

Workup

  1. washwashed successively with water, 5% sodium hydroxide solution, water, 5% hydrochloric acid solution, and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationThe resultant filtrate was concentrated under vacuum
  4. customto give a solid which
  5. customwas crystallized from dilute ethanol
  6. customto give 8.6 g

Sources & evidence

ORD record
ord-e282101106444183ba0f044e630958a4
Source dataset
uspto-grants-1976_01
Patent number
US03932168

Reaction notes

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