Benzoyl isothiocyanate → HCID 20042520, compound

HRID 1762217Notes

Reaction equation

HRID 1762217 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([CH2:16][C:17]#[CH:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[C:24]([N:32]=[C:33]=[S:34])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[C:24]([NH:32][C:33](=[S:34])[NH:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([CH2:16][C:17]#[CH:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 14368377HCID 14368377, compound

Product 1

HCID 20042520HCID 20042520, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(2-amino-6-methylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (9.3 g) in dichloromethane (140 ml) was added dropwise benzoyl isothiocyanate and the mixture was stirred for 1 hour. The solvent was evaporated under reduced pressure and the residue was triturated with ether (50 ml) to give a crystalline product. The crystals were recrystallized from ethanol to give 8-{2-[3-(benzoyl)thioureido]-6-methylbenzyloxy}-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (11.7 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was triturated with ether (50 ml)
  3. customto give a crystalline product
  4. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-5778ee49a43e4d728322b4eecdd91735
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

Loading…