Hydrochloric Acid → HCID 22350238, compound

HRID 896569Notes

Reaction equation

HRID 896569 reaction equation
[C:1]([CH2:3][C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:5])#[N:2].[CH3:16][C:17]([CH3:24])=[CH:18][C:19](OCC)=[O:20].CC(C)([O-])C.[K+].Cl>>[F:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][N:6]2[C:19](=[O:20])[CH2:18][C:17]([CH3:24])([CH3:16])[CH:3]([C:1]#[N:2])[C:4]2=[O:5])=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 12516Ethyl 3,3-dimethylacrylateHCID 11171758HCID 11171758, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22350238HCID 22350238, compoundYield 85%

Procedure

A mixture of 2-cyano-N-[2-(4-fluorophenyl)-ethyl]-acetamide (2.0 g, 19.4 mmol), ethyl 3-methylbut-2-enoate with a solution of potassium tert-butoxide in 80° C. After 16 hours, the mixture was cooled to room temperature and acidified with 1.0 N aqueous hydrochloric acid. The mixture was concentrated under vacuum to provide a brown solid. Recrystallization from 95% ethanol provided a tan solid (2.37 g, 85%). 1H NMR (300 MHz, dmso-d6) δ7.24 (m, 2H), 7.11 (t, J=9 Hz, 2H), 4.70 (s, 2H), 3.88 (m, 2H), 2.8-2.6 (m, 4H), 1.16 (s, 3H), 0.98 (s, 3H). Mass spec (ES−) m/z 287.2 (M−H−, 100%).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customto provide a brown solid
  3. customRecrystallization from 95% ethanol

Sources & evidence

ORD record
ord-9d86d4a0f3e54688b29d5521675fac8a
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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