Tetrahydrofuran → HCID 15718759, compound

HRID 2166123Notes

Reaction equation

HRID 2166123 reaction equation
N#N.C(OCC[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH2:14])[C:9]=1[NH2:15])C.[N:16]([CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]1)=[C:17]=[S:18].[O:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH2:31]([O:30][CH2:34][CH2:33][NH:14][C:10]1[C:9]([NH:15][C:17]([NH:16][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]2)=[S:18])=[CH:8][CH:13]=[CH:12][N:11]=1)[CH3:32]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 3018454Ethyl 4-isothiocyanatopiperidine-1-carboxylateHCID 86744116HCID 86744116, compound

Product 1

HCID 15718759HCID 15718759, compoundYield 73.7%

Procedure

A mixture of 25 parts of N2 -(2-ethoxyethyl)-2,3-pyridinediamine, 43 parts of ethyl 4-isothiocyanato-1-piperidinecarboxylate and 450 parts of tetrahydrofuran was stirred overnight at reflux temperature. The reaction mixture was evaporated and the residue was taken up in trichloromethane. The organic layer was washed twice with water, dried, filtered and evaporated. The residue was crystallized from a mixture of acetonitrile and 2,2'-oxybispropane. The product was filtered off and dried, yielding 35 parts (73.7%) of ethyl 4-[[[[2-[(2-ethoxyethyl)amino]-3-pyridinyl]amino]thioxomethyl]amino]-1-piperidinecarboxylate as a residue (interm. 10).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. washThe organic layer was washed twice with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from a mixture of acetonitrile and 2,2'-oxybispropane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-4a59940ce23545ae82cecab898249d7b
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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