Methanol → HCID 25065960, compound

HRID 1514850Notes

Reaction equation

HRID 1514850 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([NH2:13])[CH:7]=1)[CH3:2].[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O.CO>CS(C)=O>[CH2:1]([O:3][C:4](=[O:14])[NH:5][C:6]1[CH:11]=[CH:10][C:9]2[N:12]=[C:18]([C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[Cl:15])[NH:13][C:8]=2[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 69962-ChlorobenzaldehydeHCID 12678031HCID 12678031, compound

Product 1

HCID 25065960HCID 25065960, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A freshly prepared solution of (3,4-diamino-phenyl)-carbamic acid ethyl ester in DMSO (0.2 M, 0.10 mL) was placed in a vial. To it was added 2-chloro-benzaldehyde (0.2 M in toluene, 0.12 mL), followed by FeCl3 (0.02 M in THF, 0.050 mL). The mixture was stirred in open air at ambient temperature overnight. The mixture was then diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to give [2-(2-chloro-phenyl)-3H-benzoimidazol-5-yl]-carbamic acid ethyl ester: MS (m/z) 315.97 (M+1).

Workup

  1. extractionthe whole was loaded onto a solid phase extraction (SPE) cartridge that
  2. washWash-to-waste (5 mL MeOH)
  3. customby elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N)
  4. customafter evaporation of volatiles
  5. customthe crude was further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f6b72879c5774f5898401224022a0417
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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