Water → HCID 67360675, compound

HRID 2243342Notes

Reaction equation

HRID 2243342 reaction equation
[NH:1]1[CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:4]2[N:3]=[C:2]1[C:10]1[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:23])[C:14]=2[CH:13]=[CH:12][CH:11]=1.O>CS(C)=O>[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:23])[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 962WaterHCID 67358899HCID 67358899, compound

Product 1

HCID 67360675HCID 67360675, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
200 °C

Procedure

In a 20 ml sealed tube, dissolve 330 mg of 4-(3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-yl)-9H-fluoren-9-one, obtained in the previous stage, in 12 ml of dimethyl sulphoxide and then heat at 200° C. for one hour. After cooling, add 30 ml of water and then extract 3 times with 100 ml of ethyl acetate. The crude solid obtained is purified by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and methanol (97/3 by volume). In this way, we obtain 210 mg of 4-(4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)-9H-fluoren-9-one, in the form of a yellow powder, which is used as it is in the following stage, with the following characteristics:

Workup

  1. customIn a 20 ml sealed tube
  2. temperatureAfter cooling
  3. extractionextract 3 times with 100 ml of ethyl acetate
  4. customThe crude solid obtained
  5. customis purified by flash chromatography on silica gel (40-63 μm)
  6. washeluting with a mixture of dichloromethane and methanol (97/3 by volume)

Sources & evidence

ORD record
ord-99d599e515fb4b91b2aaef1f77952b26
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

Loading…