Carbon Disulfide → ethyl hexahydro-4-isothiocyanato-1H-azepine-1-carboxylate

HRID 704712Notes

Reaction equation

HRID 704712 reaction equation
[C:1](=[S:3])=S.[NH2:4][CH:5]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][CH2:6]1>O1CCCC1>[N:4]([CH:5]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][CH2:6]1)=[C:1]=[S:3]

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 15037323ethyl 4-aminohexahydro-1H-azepine-1-carboxylate

Product 1

HCID 15037324ethyl hexahydro-4-isothiocyanato-1H-azepine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and cooled (-10° C.) mixture of 63 parts of carbon disulfide, 52.1 parts of N,N'-methanetetraylbis[cyclohexanamine] and 360 parts of tetrahydrofuran were added dropwise 46.9 parts of ethyl 4-aminohexahydro-1H-azepine-1-carboxylate. Upon complete addition, the reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was evaporated and the residue was stirred in 2,2'-oxybispropane. The precipitate was filtered off and the filtrate was evaporated, yielding 70.75 parts (100%) of ethyl hexahydro-4-isothiocyanato-1H-azepine-1-carboxylate as a residue (interm. 29).

Workup

  1. temperaturecooled
  2. additionUpon complete addition
  3. stirringthe reaction mixture was stirred for 2 hours at room temperature
  4. customThe reaction mixture was evaporated
  5. stirringthe residue was stirred in 2,2'-oxybispropane
  6. filtrationThe precipitate was filtered off
  7. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-c0d906c3b4fc432dae52b96adb367275
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

Loading…