Ammonia → HCID 15295806, compound

HRID 865389Notes

Reaction equation

HRID 865389 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3N)=[CH:12][CH:11]=2)[C:7]2[CH:23]=[C:24]([C:28]3[N:32]([CH3:33])[C:31]4[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=4[N:29]=3)[CH:25]=[C:26]([CH3:27])[C:6]=2[N:5]=1)[CH2:2][CH3:3].N([O-])=O.[Na+].NC(N)=[O:44].[S:46](=[O:48])=[O:47].N>Cl.O.C(O)(=O)C.O.[Cu](Cl)Cl>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[S:46]([OH:44])(=[O:48])=[O:47])=[CH:12][CH:11]=2)[C:7]2[CH:23]=[C:24]([C:28]3[N:32]([CH3:33])[C:31]4[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=4[N:29]=3)[CH:25]=[C:26]([CH3:27])[C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

10

Reactant 5

HCID 222AmmoniaHCID 1119Sulfur DioxideHCID 1176UreaHCID 23668193Sodium NitriteHCID 54154472HCID 54154472, compound

Product 1

HCID 15295806HCID 15295806, compound

Reagents, catalysts & solvents 4

HCID 1621911110125-13-0CatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

9.0 g of 4'-[(2-n-Propyl-4-methyl-6-(1-methyl-benzimidazol-2-yl)-benzimidazol-1-yl)-methyl]-2-amino-biphenyl are suspended in 170 ml of 6N hydrochloric acid and at 0°-5° C. within 1 hour 1.95 g of sodium nitrite in 30 ml of water are added dropwise. Then the mixture is stirred for a further 2 hours at 0° C. and mixed with urea. The resulting solution is added dropwise at 0°-5° C. to a mixture consisting of 40 ml of a saturated solution of sulphur dioxide in glacial acetic acid and 2.25 g of copper(II)chloride-monohydrate in 3.3 ml of water. Then the mixture is stirred for a further 2 hours at ambient temperature, made alkaline with concentrated ammonia with cooling and the product precipitated is suction filtered. The filtrate is extracted with ethyl acetate and the ethyl acetate phase is concentrated by evaporation with the precipitate. After chromatography on silica gel with dichloromethane/ethanol (19:1), 4.2 g are obtained, melting point 307°-310° C.

Workup

  1. additionThe resulting solution is added dropwise at 0°-5° C. to a mixture
  2. stirringThen the mixture is stirred for a further 2 hours at ambient temperature
  3. temperaturewith cooling
  4. customthe product precipitated
  5. filtrationfiltered
  6. extractionThe filtrate is extracted with ethyl acetate
  7. concentrationthe ethyl acetate phase is concentrated by evaporation with the precipitate
  8. customAfter chromatography on silica gel with dichloromethane/ethanol (19:1), 4.2 g are obtained

Sources & evidence

ORD record
ord-197189d4cbe04b0896331108edb6b0f9
Source dataset
uspto-grants-1996_10
Patent number
US05565469

Reaction notes

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