Ammonia → HCID 20393008, compound

HRID 1862989Notes

Reaction equation

HRID 1862989 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[C:5]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:4][C:3]=1[NH2:16].[N:17]#[C:18]Br.N.C(Cl)(Cl)Cl>CO.O>[NH2:17][C:18]1[NH:16][C:3]2[CH:4]=[C:5]([O:12][CH:13]([CH3:15])[CH3:14])[C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:7][C:2]=2[N:1]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6212ChloroformHCID 10476Cyanogen BromideHCID 132301804,5-Bis[(propan-2-yl)oxy]benzene-1,2-diamine

Product 1

HCID 20393008HCID 20393008, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 1,2-diamino-4,5-di-isopropoxybenzene (2.24 g.) in methanol (40 ml.) was added to a mixture of cyanogen bromide (1.6 g.) in water (40 ml.). The mixture was stirred at 20°-25° C. for 70 hours and then basified by addition of an excess of aqueous ammonia solution (density 0.88). The mixture was then separated by filtration and the filtrate evaporated. The residue which was obtained was mixed with water (50 ml.) and chloroform (50 ml.). The chloroform phase was separated, dried (MgSO4) and evaporated. The residual gum obtained, was purified by chromatography on a column of silica gel (40 g.) using methanol-chloroform (1:3 v/v) as eluant, to give 2-amino-5,6-di-isopropoxybenzimidazole as a sticky solid (1.2 g.), having characteristic absorption bands at ν 3400, 3320, 3080, 1660 and 1565 cm-1, in the infra-red (IR) spectrum.

Workup

  1. customThe mixture was then separated by filtration
  2. customthe filtrate evaporated
  3. customThe residue which was obtained
  4. customThe chloroform phase was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residual gum obtained
  8. customwas purified by chromatography on a column of silica gel (40 g.)

Sources & evidence

ORD record
ord-74b706814d4e47a1a40de4a7bb6596e8
Source dataset
uspto-grants-1979_09
Patent number
US04167569

Reaction notes

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