Ethanol → HCID 3498159, compound

HRID 1160646Notes

Reaction equation

[C:1](#[N:10])[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1.[O:11]1CCO[CH2:13][CH2:12]1.[CH2:17]([OH:19])[CH3:18]>>[C:1](=[NH:10])([O:19][CH2:17][CH3:18])[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5](=[NH:6])[O:11][CH2:12][CH3:13])[CH:3]=1

Participants

Reactant 3

HCID 702Ethanol

HCID 12276Isophthalonitrile

HCID 312751,4-Dioxane

Product 1

HCID 3498159HCID 3498159, compound

Conditions

Temperature: 0 °C

Procedure

A suspension of isophthalonitrile (12.81 g, 100 mmol) in a mixture of dry 1,4-dioxane (100 ml)/absolute ethanol (14.6 ml) cooled to 0° C. is bubbled with HCl gas for 48 hours, during which time the temperature returns to ambient temperature. After 4 additional days of stirring, the white solid obtained (approximately 28 grams of di-chlorohydrate salt) is filtered and washed with diethyl ether. The neutralization of this salt placed in suspension in diethyl ether is carried out by slowly adding potassium an aqueous carbonate solution (30% by weight) up to basic pH. The organic phase is separated, dried on MgSO4, filtered and concentrated under reduced pressure to yield a white solid (yield>90%). δH (300 MHz, CDCl3) 1.44 (t; J 6.9; 6H), 4.32 (q; J 6.9; 4H), 7.47 (t; J 7.5; 1H), 7.86 (d; J 7.5; 2H), 8.16 (s; 1H); SM (Electrospray) m/z 221 (MH+, 100%).

Workup

customis bubbled with HCl gas for 48 hours, during which time the temperature returns to ambient temperature

Sources & evidence

ORD record: ord-f60713ed0d3d4eaeaa8bd775a7a6f9b1
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816520B2

Reaction notes

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