Potassium tert-butoxide → 9-Chloro-6-nitro-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

HRID 1628475Notes

Reaction equation

HRID 1628475 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[N:4]=[C:5]1[NH:11][CH2:10][CH2:9][CH2:8]C[NH:6]1.CC(C)([O-])C.[K+]>>[Cl:1][C:2]1[C:3]2[N:4]=[C:5]3[NH:6][CH2:8][CH2:9][CH2:10][N:11]3[C:12]=2[C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178526630HCID 178526630, compound

Product 1

HCID 1363879919-Chloro-6-nitro-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazoleYield 73%

Conditions

Temperature
60 °C

Procedure

2-Chloro-N-1,3-diazepan-2-ylidene-5-nitroaniline (5.0 g, 19.6 mmol) and potassium t-butoxide (440 mg, 3.93 mmol) were dissolved in N,N-dimethylsulfoxide (100 mL), and heated at 60° C. for 24 hr. After cooling to room temperature, to the reaction mixture was directly purified by silica gel column chromatography eluting with a 50-100% ethyl acetate/n-hexane gradient mixture to give the title compound (3.63 g, 14.3 mmol, 73%) as a yellow amorphous.

Workup

  1. temperatureAfter cooling to room temperature, to the reaction mixture
  2. customwas directly purified by silica gel column chromatography
  3. washeluting with a 50-100% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-1f47f0009dd54bf6a7b370f985d5817d
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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