Hydrochloric Acid → HCID 53806346, compound

HRID 904229Notes

Reaction equation

Cl.[OH:2][CH:3]([C:6]([CH3:20])([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[CH3:19])=[CH:10][CH:9]=1)Cl)[C:4]#[N:5].N1C=CC=CC=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].C(N(CC)CC)C>>[C:27]([O:2][C:3](=[C:6]([CH3:20])[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[CH3:19])=[CH:10][CH:9]=1)[C:4]#[N:5])(=[O:29])[CH3:28]

Participants

Reactant 5

HCID 313Hydrochloric Acid2×

HCID 1049Pyridine

HCID 7918Acetic Anhydride

HCID 8471Triethylamine

HCID 23333843HCID 23333843, compound

Product 1

HCID 53806346HCID 53806346, compoundYield 92%

Procedure

A 30-ml portion of the toluene solution containing 3.7 g (0.0145 mole) of 3-methyl-3-[4-(3-methyl-2-thienyl)phenyl]glycidonitrile obtained in (1) was saturated with dried hydrogen chloride and stirred for a further one hour so that 2-hydroxy-3-methyl-3-[4-(3-methyl-2-thienyl)phenyl]-3-chloropropionitrile may be formed. To the reaction mixture, which had been freed from the remaining hydrogen chloride by introducing dried nitrogen, was added 1.43 g (0.0181 mole) of pyridine and 1.70 g (0.0167 mole) of acetic anhydride, followed by adding 2.1 g (0.0207 mole) of triethylamine. After refluxing for 15 hours, the reaction mixture was washed with diluted hydrochloric acid, dried over anhydrous sodium sulfate, and freed from the solvent by distillation under reduced pressure to obtain 4.2 g (92% yield) of oily 2-acetoxy-3-methyl-3-[4-(3-methyl-2-thienyl)phenyl]acrylonitrile.

Workup

custommay be formed
additionby introducing dried nitrogen
temperatureAfter refluxing for 15 hours
washthe reaction mixture was washed with diluted hydrochloric acid
dry with materialdried over anhydrous sodium sulfate
distillationfreed from the solvent by distillation under reduced pressure

Sources & evidence

ORD record: ord-70e5c95c6c254983b43446900249b83b
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04230719

Reaction notes

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