Triethylamine → HCID 19855329, compound

HRID 1649931Notes

Reaction equation

HRID 1649931 reaction equation
C(N(CC)CC)C.[CH:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1)=[O:9].Cl.[NH2:20][CH2:21][C:22]#[N:23]>O1CCCC1.CN(C)C=O>[CH:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([CH:22]([NH2:23])[C:21]#[N:20])=[O:15])=[CH:12][CH:11]=1)=[O:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11491918Aminoacetonitrile hydrochlorideHCID 124246204-Formylbenzoyl chloride

Product 1

HCID 19855329HCID 19855329, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

First,12.2 g (0.12 mol) of triethylamine and then, dropwise with stirring, a solution of 10.1 g (0.06 mol) of 4-formylbenzoyl chloride in 10 ml of tetrahydrofuran are added at 0° C. to 5.6 g (0.06 mol) of 2-aminoacetonitrile hydrochloride in 50 ml of dimethylformamide at a rate such that the internal temperature does not exceed 10° C. When the addition is complete, the batch is stirred for a further 15 minutes at room temperature, poured into 400 ml of ice water and filtered, and the product thus obtained is dried. Extraction of the filtrate with 5 times 100 ml of ethyl acetate, washing the combined organic phases, drying over sodium sulphate and concentrating in vacuo yields a further fraction. In total, 8.9 g (79% of theory) of 2-(4-formylbenzoyl)-aminoacetonitrile of melting point 122°-125° C. are obtained.

Workup

  1. customdoes not exceed 10° C
  2. additionWhen the addition
  3. filtrationfiltered
  4. customthe product thus obtained
  5. customis dried
  6. extractionExtraction of the filtrate with 5 times 100 ml of ethyl acetate
  7. washwashing the combined organic phases
  8. dry with materialdrying over sodium sulphate
  9. concentrationconcentrating in vacuo
  10. customyields a further fraction

Sources & evidence

ORD record
ord-71233537968b42f38a351c511c4cab04
Source dataset
uspto-grants-1990_05
Patent number
US04921993

Reaction notes

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