Acetic Acid → HCID 22621808, compound

HRID 840099Notes

Reaction equation

HRID 840099 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]([CH3:19])[C:7]([CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=3)=[N:8][C:4]=2[CH:3]=1.[CH3:22][N:23]([CH3:32])[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.CC(O)=O.[OH-].[Na+]>C(Cl)Cl.O>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][C:7]2[N:6]([CH3:19])[C:5]3[CH:20]=[CH:21][C:2]([NH:1][CH2:28][C:27]4[CH:30]=[CH:31][C:24]([N:23]([CH3:32])[CH3:22])=[CH:25][CH:26]=4)=[CH:3][C:4]=3[N:8]=2)=[CH:12][CH:13]=1)#[N:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 74794-(Dimethylamino)BenzaldehydeHCID 14798Sodium HydroxideHCID 18763022HCID 18763022, compound

Product 1

HCID 22621808HCID 22621808, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-amino-2-[2-(4-cyanophenyl)-ethyl]-1-methyl-benzimidazole (1.0 g, 3.6 mmol) which is obtainable according to Example 2 (step c) and 4-dimethylamino-benzaldehyde (0.59 g, 3.0 mmol) in 25 mL of CH2Cl2 with 0.22 mL of AcOH are combined with Na[HB(OAc)3](2.2 g, 10.3 mmol) at ambient temperature with stirring. The mixture is stirred for 1 h at ambient temperature, covered with water, carefully acidified with conc hydrochloric acidaq and then made alkaline with 4N NaOH solution. The organic phase is separated off, dried and concentrated by evaporation. The product is chromatographed over silica gel (CH2Cl2/methanol=5/1) and crystallised from ethyl acetate.

Workup

  1. stirringThe mixture is stirred for 1 h at ambient temperature
  2. customThe organic phase is separated off
  3. customdried
  4. concentrationconcentrated by evaporation
  5. customThe product is chromatographed over silica gel (CH2Cl2/methanol=5/1)
  6. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-16b9f6a3f5f14b0a8d3c8067407cdc8b
Source dataset
uspto-grants-2002_04
Patent number
US06365584B1

Reaction notes

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