1,1-Dichloroethane → HCID 9868630, compound

HRID 1370607Notes

Reaction equation

HRID 1370607 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:18][NH:19][CH:20]([CH3:22])[CH3:21])=[C:5]([CH3:23])[CH:4]=1.[CH3:24][C:25]1[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[C:26]=1[C:27](Cl)=[O:28].ClC(Cl)C>C(=O)([O-])[O-].[Na+].[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:18][N:19]([CH:20]([CH3:21])[CH3:22])[C:27]([C:26]2[C:25]([CH3:24])=[CH:33][C:32]([CH3:34])=[CH:31][C:30]=2[CH3:35])=[O:28])=[C:5]([CH3:23])[CH:4]=1

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 970382,4,6-Trimethylbenzoyl chlorideHCID 11738409HCID 11738409, compound

Product 1

HCID 9868630HCID 9868630, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

A solution of 3 g (10.5 mmole) 1-[2-(chloromethyl)benzimidazolyl]-4-methoxy-2-methylbenzene in 20 mL of dry acetonitrile is treated with 5 mL of isopropylamine for 1 hour in a sealed reaction vessel at 50° C. The solvent is removed in vacuo and the residue is partitioned between 30 mL of ethyl acetate and 10 mL of 1 N NaOH. The ethyl acetate layer is dried over anhydrous Na2SO4 and solvent removed in vacuo to afford 3.1 g (98%) {[1-(4-methoxy-2-methylphenyl)benzimidazol-2-yl]methyl}(methylethyl)amine. The latter amine is then vigorously stirred with 2.6 mL of 2,4,6-trimethylbenzoylchloride in a 1:1 mixture of dichloroethane and saturated aqueous sodium carbonate (30 mL) at room temperature for 1 hour. The mixture is partitioned, the organic layer is dried with Na2SO4 and the solvent removed in vacuo. The crystallized product is triturated in ethyl ether, filtered and dried to afford 4.4 g (92%) of white solid N-{[1-(4-methoxy-2-methylphenyl)benzimidazol-2-yl]methyl}-N-(methylethyl)(2,4,6-trimethylphenyl)carboxamide: Mass Spec. 456 (M+H); (Compound 1).

Workup

  1. customThe mixture is partitioned
  2. dry with materialthe organic layer is dried with Na2SO4
  3. customthe solvent removed in vacuo
  4. customThe crystallized product is triturated in ethyl ether
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-c444b38c66f947f191fca70e2e1aa5d7
Source dataset
uspto-grants-2003_06
Patent number
US06583169B2

Reaction notes

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