Methyl iodide → HCID 10253961, compound

HRID 488738Notes

Reaction equation

HRID 488738 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]23[CH2:24][CH2:23][CH2:22][CH:21]=[C:8]2[N:9]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[C:10](=[O:12])[NH:11]3)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:29]I>CN(C=O)C>[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]23[CH2:24][CH2:23][CH2:22][CH:21]=[C:8]2[N:9]([C:13]2[CH:14]=[C:15]([Cl:20])[CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:10](=[O:12])[N:11]3[CH3:29])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9846654HCID 9846654, compound

Product 1

HCID 10253961HCID 10253961, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3a-(4-Bromo-benzyl)-1-(3,5-dichlorophenyl)-1,3,3a,4,5,6-hexahydro-benzimidazol-2-one (3.0 g) (0.0066 mol) in DMF (50 ml) was carefully dropped on a suspension of NaH 60% (0.32 g) (1.2 eq) in DMF (20 ml) at RT. The reaction mixture was stirred 1 h at RT then methyl iodide (0.6 ml) (1.5 eq) was added. After one night, the reaction mixture was partitioned between water and tBuOMe. The obtained precipitate was filtered, washed with water and tBuOMe, and dried to give 3a-(4-Bromo-benzyl)-1-(3,5-dichlorophenyl)-3-methyl-1,3,3a,4,5,6-hexahydro-benzimidazol-2-one (1.8 g) as a white solid. 1H NMR (CDCl3): 7.39 (2H, d), 7.10 (1H, m), 7.0 (2H, d), 6.77 (2H, m), 4.90 (1H, m), 3.0 (3H, s), 2.95 (2H, s), 2.5-2.2 (2H, m), 2.2-1.9 (3H, m), 1.8-1.6 (1H, m).

Workup

  1. waitAfter one night
  2. customthe reaction mixture was partitioned between water and tBuOMe
  3. filtrationThe obtained precipitate was filtered
  4. washwashed with water and tBuOMe
  5. customdried

Sources & evidence

ORD record
ord-6e0d2caf288b43fa94160f4d5fe3fcd9
Source dataset
uspto-grants-2005_12
Patent number
US06974815B2

Reaction notes

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