Sodium Chloride → HCID 178437414, compound

HRID 233004Notes

Reaction equation

HRID 233004 reaction equation
[CH2:1]([C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]#[N:22])=[CH:11][CH:10]=2)[C:6]2[CH:23]=[C:24]([C:28]3[N:32]([CH3:33])[C:31]4[CH:34]=[CH:35][C:36]([F:38])=[CH:37][C:30]=4[N:29]=3)[CH:25]=[C:26]([CH3:27])[C:5]=2[N:4]=1)[CH3:2].[Cl-].[NH4+].[N-:41]=[N+:42]=[N-:43].[Na+].[Cl-].[Na+]>CN(C)C=O>[CH2:1]([C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:43][N:42]=[N:41][N:22]=3)=[CH:11][CH:10]=2)[C:6]2[CH:23]=[C:24]([C:28]3[N:32]([CH3:33])[C:31]4[CH:34]=[CH:35][C:36]([F:38])=[CH:37][C:30]=4[N:29]=3)[CH:25]=[C:26]([CH3:27])[C:5]=2[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 19964827HCID 19964827, compound

Product 1

HCID 178437414HCID 178437414, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.9 g (3.8 mMol) of 4'-[(2-ethyl-4-methyl-6-(1-methyl-5-fluoro-benzimidazol-2-yl)-benzimidazol-1-yl)-methyl]-2-cyano-biphenyl, 4.1 g (76 mMol) of ammonium chloride and 4.9 g (76 mMol) of sodium azide in 30 ml of dimethylformamide is heated to 140° C. for 15 hours, then a further 2.0 g of ammonium chloride and 2.4 g of sodium azide are added and the mixture is heated for another 4 hours to 140° C. Then the solution is stirred into about 80 ml of saturated sodium chloride solution, the crude product precipitated is suction filtered and purified by column chromatography (150 g of silica gel; eluant: methylene chloride/ethanol=19:1).

Workup

  1. temperaturethe mixture is heated for another 4 hours to 140° C
  2. customthe crude product precipitated
  3. filtrationfiltered
  4. custompurified by column chromatography (150 g of silica gel; eluant: methylene chloride/ethanol=19:1)

Sources & evidence

ORD record
ord-e8f50f3fa7ab4f198ae92d31a216dfb2
Source dataset
uspto-grants-1997_01
Patent number
US05591762

Reaction notes

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