Water → HCID 18780696, compound

HRID 1421274Notes

Reaction equation

HRID 1421274 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][N:14]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]3=[O:23])=[CH:9][CH:8]=2)[N:3]=1.[H-].[Na+].Br[CH2:27][CH2:28][Cl:29].O>CN1CCCC1=O>[Cl:29][CH2:28][CH2:27][N:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:14]([CH2:13][C:10]2[CH:9]=[CH:8][C:7]([C:4]3[N:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[CH:12][CH:11]=2)[C:15]1=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 18780704HCID 18780704, compound

Product 1

HCID 18780696HCID 18780696, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

1-[4-(5-Methyl-1,2,4-oxadiazol-3-yl)phenyl]methyl-1,3-dihydro-2H-benzimidazol-2-one (0.416 g, 1.36 mmol) was added to a suspension of 60% sodium hydride (0.06 g, 1.49 mmol, dispersion in oil) in N-methylpyrrolidinone (3 ml) and stirred for 2 hours. More N-methylpyrrolidinone (2 ml) was added followed by 1-bromo-2-chloroethane (0.203 ml, 0.351 g, 2.44 mmol). The resultant mixture was allowed to stir at room temperature for 16 h then water was added and the mixture extracted with ethyl acetate (2×30 ml). The organic layer was washed with water (4×50 ml), brine (50 ml), dried (MgSO4).filtered and evaporated in vacuo to give a light brown oil.

Workup

  1. stirringto stir at room temperature for 16 h
  2. extractionthe mixture extracted with ethyl acetate (2×30 ml)
  3. washThe organic layer was washed with water (4×50 ml), brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customto give a light brown oil

Sources & evidence

ORD record
ord-dbd05aaa600849f5bc7e824822ebbaac
Source dataset
uspto-grants-2000_06
Patent number
US06075039

Reaction notes

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