Cyclohexanol → 5-Cyclohexyloxy-2-carbomethoxyaminobenzimidazole

HRID 2398733

Reaction equation

HRID 2398733 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[H][H].[N+:12]([C:15]1[CH:21]=[CH:20][C:19](Cl)=[CH:18][C:16]=1[NH2:17])([O-])=O.[C:23]([NH:27][C:28]#N)([O:25][CH3:26])=[O:24]>CN(C)C=O>[CH:1]1([O:7][C:19]2[CH:20]=[CH:21][C:15]3[N:12]=[C:28]([NH:27][C:23]([O:25][CH3:26])=[O:24])[NH:17][C:16]=3[CH:18]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 742185-Chloro-2-nitroanilineHCID 89023Methyl N-cyanocarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 202844345-Cyclohexyloxy-2-carbomethoxyaminobenzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of cyclohexanol (0.03 mol) in 75 ml. of dry dimethylformamide under nitrogen is agitated while 55% sodium hydride (0.03 mol) in oil is added portionwise. When evolution of hydrogen ceases 2-nitro-5-chloroaniline (0.025 mol) is added with stirring. The mixture is warmed at 75°-80° C. for 1 hour then poured onto 6 volumes of ice slurry. The separated product recrystallized from water to give red crystals of the nitroaminobiphenylether. After hydrogenation and reaction with carbomethoxycyanamide as described above the product, 5-cyclohexyloxy-2-carbomethoxyaminobenzimidazole is obtained.

Workup

  1. additionis added portionwise
  2. temperatureThe mixture is warmed at 75°-80° C. for 1 hour
  3. additionthen poured onto 6 volumes of ice slurry
  4. customThe separated product recrystallized from water
  5. customto give red crystals of the nitroaminobiphenylether

Sources & evidence

ORD record
ord-1c5f0135e69a40848c0e08e99d8c8114
Source dataset
uspto-grants-1977_05
Patent number
US04025638

Linked notes

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