Hydrochloric Acid → HCID 178468760, compound

HRID 653720Notes

Reaction equation

HRID 653720 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[CH:30]([CH3:32])[CH3:31])=[CH:11][CH:10]=1)#[N:2].[N-:33]=[N+:34]=[N-:35].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C.O>[CH:30]([C:17]1[N:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]3[NH:35][N:34]=[N:33][N:2]=3)=[CH:14][CH:13]=2)[C:20]2[C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=1)([CH3:31])[CH3:32]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 15654659HCID 15654659, compound

Product 1

HCID 178468760HCID 178468760, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-isopropylbenzimidazole-7-carboxylate (2.12 g), sodium azide (3.9 g) and ammonium chloride (3.2 g) in DMF (15 ml) was stirred for 5 days at 110°-120 C. To the reaction mixture was added water (150 ml), which was made acidic (pH 3-4) with dilute hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated to dryness. The concentrate was crystallized from ethanol to afford colorless prisms (1.2 g, 52%), m.p. 144°-146° C.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated to dryness
  5. customThe concentrate was crystallized from ethanol

Sources & evidence

ORD record
ord-0c3ada84a2c44cb5b2d76f8c7bfbb010
Source dataset
uspto-grants-1992_07
Patent number
US05128356

Reaction notes

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