107819-90-9 → HCID 86646935, compound

HRID 1929340Notes

Reaction equation

HRID 1929340 reaction equation
CS/[C:3](/[NH:12][C:13](=O)OC(C)(C)C)=[N:4]\[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[Cl:20][C:21]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:22]=1[CH2:23][O:24][C:25]1[CH:26]=[C:27]([NH2:32])C(N)=[CH:29][CH:30]=1>CO.C(O)(=O)C>[Cl:20][C:21]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:22]=1[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:13]2[N:12]=[C:3]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[NH:32][C:27]=2[CH:26]=1

Participants

5

Reactant 2

HCID 6376008107819-90-9HCID 68511467HCID 68511467, compound

Product 1

HCID 86646935HCID 86646935, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

add 615 mg of bis(1,1-dimethylethyl) [(Z)-(methylsulphanyl)methylylidene]biscarbamate to a solution of 600 mg of 4-[(2,6-dichlorobenzyl)oxy]benzene-1,2-diamine in a mixture of 30 cm3 of methanol and 127 mg of pure acetic acid. The mixture is refluxed for about 3 hours then concentrated under reduced pressure (0.2 kPa). The residue is taken up in 20 cm3 of a saturated aqueous solution of potassium carbonate and the mixture is extracted three times with 100 cm3 of dichloromethane. The combined organic phases are dried over magnesium sulphate, then filtered and evaporated under reduced pressure. After purification of the residue by silica-column flash chromatography [eluent: dichloromethane/methanol (98/2 by volume)], we obtain 586 mg of 1,1-dimethylethyl {6-[(2,6-dichlorobenzyl)oxy]-1H-benzimidazol-2-yl}carbamate in the form of an orange resin, which has the following characteristics:

Workup

  1. temperatureThe mixture is refluxed for about 3 hours
  2. concentrationthen concentrated under reduced pressure (0.2 kPa)
  3. extractionthe mixture is extracted three times with 100 cm3 of dichloromethane
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customAfter purification of the residue by silica-column flash chromatography [eluent: dichloromethane/methanol (98/2 by volume)], we

Sources & evidence

ORD record
ord-32f46420833d4d768ba7cd58eb7cf23b
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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