Ethanol → HCID 67916611, compound

HRID 1197112Notes

Reaction equation

HRID 1197112 reaction equation
[C:1]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:16]=[CH:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[N:12](C(=O)CCl)[C:11]=2[CH:25]=1)([O:3][CH2:4][CH3:5])=[O:2].[CH3:26][NH2:27].[CH2:28]([OH:30])[CH3:29]>>[C:1]([NH:6][C:7]1[CH:8]=[C:9]([C:28](=[O:30])[CH3:29])[C:10]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[N:12]([NH:27][CH3:26])[C:11]=2[CH:25]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 14986153HCID 14986153, compound

Product 1

HCID 67916611HCID 67916611, compound

Procedure

12 g, 0.033 moles of 3-carbethoxyamino-5-chloroacetyl-5H-dibenz[b,f]azepine (hereafter referred to as "Startazepine 5") is suspended in 150 ml of ethanol. About 50 ml of an approximately 35% aqueous methylamine solution (about 0.5 moles of CH3NH2) are added and the mixture is stirred for 5 hours at 50° C. to 60° C., a clear, light yellow solution is formed. The reaction mixture is concentrated under vacuum to half the volume and then mixed with copious amounts of water. The oily precipitated base is extracted with chloroform (2×50 ml) and the organic phase is washed with water, dried over sodium sulfate and distilled to dryness under vacuum. A crystalline mass remains, which melts at 148° C. to 153° C., representing a yield of 7.2 g.

Workup

  1. customa clear, light yellow solution is formed
  2. concentrationThe reaction mixture is concentrated under vacuum to half the volume
  3. additionmixed with copious amounts of water
  4. extractionThe oily precipitated base is extracted with chloroform (2×50 ml)
  5. washthe organic phase is washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationdistilled to dryness under vacuum

Sources & evidence

ORD record
ord-f9a344eac9bf43cfb30080a2a75c483b
Source dataset
uspto-grants-1992_05
Patent number
US05116974

Reaction notes

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