Sodium Sulfide → HCID 178522503, compound

HRID 1091538Notes

Reaction equation

HRID 1091538 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:8]([CH2:22][CH2:23][N:24]=3)[C:9]([NH:13][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=3)=[N:10][C:11]=2[CH:12]=1.[S-2].[Na+].[Na+]>CN1CCCC1=O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:8]([CH2:22][CH2:23][N:24]=3)[C:9]([NH:13][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=3)=[N:10][C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 178487302HCID 178487302, compound

Product 1

HCID 178522503HCID 178522503, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

A suspension of N-(8-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide (example 2-22) 3.50 g (10.9 mmol) and sodium sulfide 4.25 g (54.5 mmol) in 1-methyl-2-pyrrolidinone 10 mL was heated to 160° C. for 4 hours (LC -MS indicated complete consumption of the starting material). The mixture was cooled to room temperature and volatile side products were evaporated. The mixture was partitioned between chloroform and 0.5N NaOH solution. The aqueous layer was neutralized and the formed precipitate was collected to give the title compound 2.34 g as off-white solid. Yield 69.9%.

Workup

  1. customconsumption of the starting material)
  2. temperatureThe mixture was cooled to room temperature
  3. customvolatile side products were evaporated
  4. customThe mixture was partitioned between chloroform and 0.5N NaOH solution
  5. customthe formed precipitate was collected

Sources & evidence

ORD record
ord-e965b4cea772475db2efea941d84d7a3
Source dataset
uspto-grants-2012_03
Patent number
US08129386B2

Reaction notes

Loading…