Sodium Carbonate → HCID 11268197, compound

HRID 636848Notes

Reaction equation

HRID 636848 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Cs+].[Cs+].[C:28]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([SH:38])=[CH:34][CH:33]=1)(=[O:30])[CH3:29]>CN1C(=O)CCC1.O>[C:14]([C:8]1([C:4]2[CH:3]=[C:2]([S:38][C:35]3[CH:34]=[CH:33][C:32]([NH:31][C:28](=[O:30])[CH3:29])=[CH:37][CH:36]=3)[CH:7]=[CH:6][CH:5]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:15]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 707774'-MercaptoacetanilideHCID 114597874-(3-bromophenyl)oxane-4-carbonitrile

Product 1

HCID 11268197HCID 11268197, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

4-(3-Bromo-phenyl)-tetrahydro-pyran-4-carbonitrile (1.33 g) was mixed with Na2CO3 (1.59 g), Cs2CO3 (0.651 g) and 4-acetamidothiophenol (1 g) in N-methyl pyrrolidinone (15 mL). The reaction mixture was heated at 130° C. overnight. After cooling, the mixture was poured into iced water. The product precipitated out as a solid, was collected by suction filtration. The solid was recrystallized from a mixture of EtOAc and hexanes to provide N-{4-[3-(4-Cyano-tetrahydro-pyran-4-yl)-phenyl sulfanyl]-phenyl}acetamide(1.4 g, 80% yield).

Workup

  1. temperatureAfter cooling
  2. customThe product precipitated out as a solid
  3. filtrationwas collected by suction filtration
  4. customThe solid was recrystallized from a mixture of EtOAc and hexanes

Sources & evidence

ORD record
ord-9ded8e0aed3a47f39624ba2673d022a8
Source dataset
uspto-grants-2001_02
Patent number
US06194585B1

Reaction notes

Loading…