Sodium Hydroxide → HCID 69134440, compound

HRID 969516Notes

Reaction equation

HRID 969516 reaction equation
[Br:1][C:2]1[C:3]([CH2:14][CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:4]([NH2:13])[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1.[OH-].[Na+]>P(=O)(O)(O)O>[Br:1][C:2]1[C:3]2[CH2:14][CH2:15][CH:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:13][C:4]=2[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69135061HCID 69135061, compound

Product 1

HCID 69134440HCID 69134440, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
130 °C

Procedure

A suspension of 2.0 g (5.6 mmol) 6-bromo-1,2-dimethyl-5-(3-phenyl-allyl)-1H-benzimidazol-4-ylamine in 10 ml phosphoric acid (85%) was heated to 130° C. for 20 min. The solution was poured onto crushed ice and the pH adjusted to pH=9 by the addition of 6N sodium hydroxide solution. The mixture was extracted with dichloromethane/methanol (10:1), the organic phase was separated, dried over anhydrous magnesium sulphate and evaporated. The residue was purified by column chromatography on silica gel (toluene/dioxane/methanol=6:3.8:02). Crystallization from diisopropyl ether yielded 1.7 g (84%) of the title compound as a colourless solid. m.p. 206-210° C.

Workup

  1. additionThe solution was poured
  2. customonto crushed ice
  3. extractionThe mixture was extracted with dichloromethane/methanol (10:1)
  4. customthe organic phase was separated
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (toluene/dioxane/methanol=6:3.8:02)
  8. customCrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-9ade5f3a375e4247b64fca16f0d550ef
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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