Dimethyl Sulfoxide → HCID 67895934, compound

HRID 1460516Notes

Reaction equation

HRID 1460516 reaction equation
[C:1]([CH:3]([CH:9]1[CH2:15][CH2:14][CH2:13][N:12](C(OCC)=O)[CH2:11][CH2:10]1)C(OCC)=O)#[N:2].[CH3:21]S(C)=O.[OH2:25].[CH2:26]([OH:28])[CH3:27]>>[C:1]([CH2:3][CH:9]1[CH2:15][CH2:14][CH2:13][NH:12][CH:11]([C:21]([O:28][CH2:26][CH3:27])=[O:25])[CH2:10]1)#[N:2]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 702EthanolHCID 962WaterHCID 15037319HCID 15037319, compound

Product 1

HCID 67895934HCID 67895934, compound

Procedure

A mixture of 84.6 parts of ethyl α-cyano-1-(ethoxycarbonyl)hexahydro-1H-azepine-4-acetate, 300 parts of dimethyl sulfoxide and 15 parts of water was stirred and heated for 5 hours in an oil bath at 150° C. while ethanol was distilled off. The excess of dimethyl sulfoxide was distilled off and the residue was taken up in water. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was distilled at 13.30 Pa, yielding 43.2 (66.5%) of ethyl 4-(cyanomethyl)hexahydro-1H-azepinecarboxylate; bp. 125° C. (int. 25).

Workup

  1. distillationwas distilled off
  2. distillationThe excess of dimethyl sulfoxide was distilled off
  3. extractionThe product was extracted with dichloromethane
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe residue was distilled at 13.30 Pa

Sources & evidence

ORD record
ord-e40d216bb89548ea8319cc79dda8e4cd
Source dataset
uspto-grants-1991_12
Patent number
US05071846

Reaction notes

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