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

HRID 1937047Notes

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 wive the desired amine product.

Sources & evidence

ORD record: ord-c9c40cf26e254306899b24a35900fa4f
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06392049B1

Reaction notes

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