Carbon Disulfide → HCID 15718941, compound

HRID 2166142Notes

Reaction equation

HRID 2166142 reaction equation
[C:1](=[S:3])=S.[CH2:4]([O:6][CH2:7][CH2:8][N:9]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=[C:10]1[CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH2:27])[CH2:21][CH2:20]1)[CH3:5]>O1CCCC1>[CH2:4]([O:6][CH2:7][CH2:8][N:9]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=[C:10]1[CH2:18][CH:19]1[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][N:27]=[C:1]=[S:3])[CH2:23][CH2:24]1)[CH3:5]

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 15718932HCID 15718932, compound

Product 1

HCID 15718941HCID 15718941, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and cooled (-10° C.) mixture of 15 parts of carbon disulfide, 6.2 parts of N,N-methanetetraylbis[cyclohexanamine] and 90 parts of tetrahydrofuran was added dropwise a solution of 8.6 parts of 4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperidineethanamine in tetrahydrofuran. Upon complete addition, the reaction mixture was stirred for 1 hour at room temperature. The whole was evaporated, yielding 11.2 parts (100%) of 3-(2-ethoxyethyl)-2-[[1-(2-isothiocyanatoethyl)-4-piperidinyl]methyl]-3H-imidazo[4,5-b]pyridine as a residue (compound 136).

Workup

  1. temperaturecooled
  2. additionUpon complete addition
  3. stirringthe reaction mixture was stirred for 1 hour at room temperature
  4. customThe whole was evaporated

Sources & evidence

ORD record
ord-e46cf7522884443b9edd86e71385b2ff
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

Loading…