3-Aminopropionitrile → n-(2-cyanoethyl)benzamide

HRID 381685Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][C:13]#[N:14]>>[C:1]([NH:14][CH2:13][CH2:12][C:11]#[N:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 16473-Aminopropionitrile

HCID 7412Benzoyl chloride

Product 1

HCID 284729n-(2-cyanoethyl)benzamide

Procedure

Benzoyl chloride and aminoethylcyanide are reacted to give N-benzoyl-aminoethylcyanide, which is reacted with hydrogen sulfide in ammonia to yield the thioamide, which is reacted with an appropriate a-halo ketone to yield the desired thiazole. Treatment with 5N hydrochloric acid removes the protecting benzoyl group to give the desired amine product.

Sources & evidence

ORD record: ord-8f345e5ce26b49f38dd0077c107aab8b
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06307054B1

Reaction notes

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