Ethanol → HCID 178456492, compound

HRID 1638330Notes

Reaction equation

HRID 1638330 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[NH:8][C:7]([C:14]3[CH:24]=[CH:23][C:17](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])=[CH:16][CH:15]=3)=[N:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28].S(=O)(=O)(O)O.[CH2:34](O)[CH3:35]>>[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[NH:8][C:7]([C:14]3[CH:24]=[CH:23][C:17](/[CH:18]=[CH:19]/[C:20]([O:22][CH2:34][CH3:35])=[O:21])=[CH:16][CH:15]=3)=[N:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 178456490HCID 178456490, compound

Product 1

HCID 178456492HCID 178456492, compound

Procedure

A suspension of (E)-4-(1,2,3,6-tetrahydro-2,6-dioxo-1,3,-dipropyl-9H-purin-8-yl)cinnamic acid (4.00 g, 10.4mmol) (Example 6) and concentrated sulfuric acid (1 ml) in absolute ethanol (1.5 L) was refluxed for 2 hours with slow distillation of 75 ml of vapor. Reflux was continued for 3 days with exclusion of moisture with 50 ml distillate being removed during the final 4 hours. The cooled suspension was filtered to yield ethyl (E)-4-(1,2,3,6-tetrahydro-2,6-dioxo-1,3-dipropyl-9H-purin-8-yl)cinnamate as a pale yellow solid. mp >300° C. Analysis for (C22H26N4O4). C,64.38; H,6.38; N,13.65. Found: C, 64.34; H, 6.43; N, 13.63.

Workup

  1. temperaturewas refluxed for 2 hours with slow distillation of 75 ml of vapor
  2. temperatureReflux
  3. custombeing removed during the final 4 hours
  4. filtrationThe cooled suspension was filtered

Sources & evidence

ORD record
ord-59365f7a66374a35a932cbeb8d10c189
Source dataset
uspto-grants-1989_11
Patent number
US04879296

Reaction notes

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