Maleic Acid → 4-[5-(2-methoxyphenoxy)pentoxy]benzenecarboximidamide (Z)-2-butenedioate

HRID 6074Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[NH:20])[NH2:19])=[CH:14][CH:13]=1.[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29]>C(O)C>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29].[CH3:1][O:2][C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18](=[NH:19])[NH2:20])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 55 °C

Procedure

4-[5-(2-Methoxyphenoxy)pentoxy]benzenecarboximidamide is dissolved in ethanol (2 B anhydrous, 9.6 L) with warming to 55° C. and this solution is filtered into a 10 gallon resin flask. The filtrate whose temperature is now 50° C. is admixed with a warm (~45° C.), filtered solution of maleic acid (0.488 kg, 4.20 mol) in 2 B anhydrous ethanol (4.15 L) rapidly. The product precipitates almost immediately and temperature rises to approximately 60°-65° C. The mixture is cooled to 5° C. with an ice bath for 2 hours and then filtered. The filter cake is washed with 2 B anhydrous ethanol (2×1 L) and then dried in vacuo (71° C., 3 mm Hg) for 16 hours to yield 4-[5-(2-methoxyphenoxy)pentoxy]benzenecarboximidamide (Z)-2-butenedioate, m.p. 163°-165° C.

Workup

filtrationthis solution is filtered into a 10 gallon resin flask
customis now 50° C.
temperaturea warm (~45° C.)
customThe product precipitates almost immediately
customrises to approximately 60°-65° C
temperatureThe mixture is cooled to 5° C. with an ice bath for 2 hours
filtrationfiltered
washThe filter cake is washed with 2 B anhydrous ethanol (2×1 L)
customdried in vacuo (71° C., 3 mm Hg) for 16 hours

Sources & evidence

ORD record: ord-f556ac80422c467dab5bec5fa4cf8285
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246965

Reaction notes

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