Hydrochloric Acid → HCID 18762991, compound

HRID 431073Notes

Reaction equation

HRID 431073 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.[CH:22]1[CH:27]=[C:26]2[CH:28]=[CH:29][CH:30]=[C:31]([CH:32]=O)[C:25]2=[CH:24][CH:23]=1.Cl.[OH-].[Na+]>ClCCl.O.C(O)(=O)C>[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][CH2:32][C:31]4[C:25]5[C:26](=[CH:27][CH:22]=[CH:23][CH:24]=5)[CH:28]=[CH:29][CH:30]=4)=[CH:3][C:4]=3[N:8]=2)=[CH:12][CH:13]=1)#[N:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 61951-NaphthaldehydeHCID 14798Sodium HydroxideHCID 18763022HCID 18763022, compound

Product 1

HCID 18762991HCID 18762991, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.0 g (3.6 mmol) of 5-amino-2-[2-(4-cyanophenyl)-ethyl]-1-methyl-benzimidazole and 1-naphthylaldehyde (0.33 mL, 3.6 mmol) are combined with 0.22 mL acetic acid in 25 mL of dichloromethane at ambient temperature and Na[HB(Oac)3] is added thereto with stirring. The mixture is stirred for 1 h at ambient temperature, covered with water, carefully acidified with concentrated aqueous hydrochloric acid and then made alkaline with 4N NaOH solution. The organic phase is separated off, dried and evaporated down. The product is chromatographed over silica gel and optionally crystallised from diethyl ether.

Workup

  1. stirringThe mixture is stirred for 1 h at ambient temperature
  2. customThe organic phase is separated off
  3. customdried
  4. customevaporated down
  5. customThe product is chromatographed over silica gel
  6. customoptionally crystallised from diethyl ether

Sources & evidence

ORD record
ord-dfc755e245b84fd5af070ec1300444c2
Source dataset
uspto-grants-2003_12
Patent number
US06656956B2

Reaction notes

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