Water → HCID 178463202, compound

HRID 1765965Notes

Reaction equation

HRID 1765965 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[C:10](=[N:12]/[C:13]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:17][CH:16]=[CH:15][C:14]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)/[CH3:11].C([O-])([O-])=O.[K+].[K+].[CH2:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.O>CN(C=O)C>[CH2:37]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[C:10](=[N:12]/[C:13]1[C:14]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:15][CH:16]=[CH:17][C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)/[CH3:11])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178463203HCID 178463203, compound

Product 1

HCID 178463202HCID 178463202, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.70 g (1.87 mmol) N-[(1E)-1-(1H-benzimidazol-2-yl)ethylidene]-N-1,1′:3′,1″-terphenyl-2′-ylamine, 1.42 g (10.3 mmol) anhydrous K2CO3 and 0.35 g (2.06 mmol) benzylbromide in 4 ml anhydrous DMF was stirred at room temperature for 10 hours. The reaction mixture was then poured into 80 ml water, stirred for 10 min and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water (3×25 ml) and dried over anhydrous Na2SO4. The solvent was evaporated to give an yellow oil which was triturated with 5 ml methanol at −78° C., filtered while cold washed with cold (−78° C.) methanol (2×2 ml) and dried under reduced pressure. Yield 0.56 g (66.2%). 1H NMR (250 MHz, CDCl3), δ, ppm: 2.07 (s, 3H), 5.51 (m, 2H), 6.90 (m, 2H), 7.22 (m, 19H), 7.78 (m, 1H).

Workup

  1. stirringstirred for 10 min
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe combined extracts were washed with water (3×25 ml)
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated
  6. customto give an yellow oil which
  7. customwas triturated with 5 ml methanol at −78° C.
  8. filtrationfiltered
  9. washwhile cold washed with cold (−78° C.) methanol (2×2 ml)
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-bd87bc362e384023a473892f4a7c1028
Source dataset
uspto-grants-2007_06
Patent number
US07229943B2

Reaction notes

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