3-Ethoxy-2-propenoyl chloride → HCID 67205344, compound

HRID 472159

Reaction equation

[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH:6]=1.[CH2:14]([O:16][CH:17]=[CH:18][C:19](Cl)=[O:20])[CH3:15]>N1C=CC=CC=1>[CH2:14]([O:16][CH:17]=[CH:18][C:19]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([N:5]2[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]2)=[CH:8][CH:9]=1)=[O:20])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

4-(4-methyl-1H-imidazol-1-yl)aniline (15 g, 138 mmol) was dissolved in dry pyridine (80 mL), freshly distilled 3-ethoxyacryloyl chloride (19 g, 140 mmol) was then added drop-wise at 5°/0° C. The resulting mixture was stirred at 0° C. for 1 hours and at r.t. overnight. The reaction mixture was quenched with water (500 mL), the pH was adjusted to pH=10, by adding K2CO3 and the resulting solid was filtered, washed with water and dried, to provide the title product as slight orange powder (18.6 g; 75%), m.p.: 214-216° C. C15H17N3O2, MW: 271.32.

Workup

customThe reaction mixture was quenched with water (500 mL)
additionby adding K2CO3
filtrationthe resulting solid was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-70d0fd609848416c9eb2ed7ffc069626
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633208B2

Linked notes

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