Hydrochloric Acid → HCID 19833133, compound

HRID 1639397Notes

Reaction equation

HRID 1639397 reaction equation
Cl.[Cl:2][C:3]1[CH:21]=[CH:20][C:6]2[C:7](=[O:19])[CH2:8][CH2:9][CH2:10][N:11]([C:16]([NH2:18])=[O:17])[C:12](=[O:15])[CH2:13][CH2:14][C:5]=2[CH:4]=1.[CH2:22]([OH:24])[CH3:23]>>[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([C:7](=[O:19])[CH2:8][CH2:9][CH2:10][NH:11][C:16]([NH2:18])=[O:17])=[C:5]([CH:4]=1)[CH2:14][CH2:13][C:12]([O:24][CH2:22][CH3:23])=[O:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 19833162HCID 19833162, compound

Product 1

HCID 19833133HCID 19833133, compound

Procedure

7 ml of concentrated hydrochloric acid are added to a solution of 6.80 g (0.023 mol) of 11-chloro-2,3,5,6,7,8-hexahydro-3,8-dioxo-4-benzazecine-4(1H)-carboxamide in 5 l of ethanol and the mixture is stirred at room temperature for 13 days. The solution is concentrated, extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Chromatography on silica gel with methylene chloride/methanol (97:3) and crystallization from ethyl acetate/hexane gives ethyl 5-chloro-2-(4-ureidobutyryl)hydrocinnamate as white crystals with melting point 127°-129°.

Workup

  1. concentrationThe solution is concentrated
  2. extractionextracted with methylene chloride/water
  3. dry with materialdried with magnesium sulfate
  4. distillationthe solvent is distilled in a vacuum
  5. customChromatography on silica gel with methylene chloride/methanol (97:3) and crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1c78f9ed772647a09f5b466646a02db0
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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