34840-23-8 → HCID 86646931, compound

HRID 1929334Notes

Reaction equation

HRID 1929334 reaction equation
CO[C:3](=O)[NH:4]/[C:5](/SC)=[N:6]/[C:7](=[O:10])[O:8][CH3:9].[Cl:14][C:15]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:16]=1[CH2:17][O:18][C:19]1[CH:20]=[C:21]([NH2:26])C(N)=[CH:23][CH:24]=1>CO.C(O)(=O)C>[Cl:14][C:15]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:16]=1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:3]2[N:4]=[C:5]([NH:6][C:7](=[O:10])[O:8][CH3:9])[NH:26][C:21]=2[CH:20]=1

Participants

5

Reactant 2

HCID 600013434840-23-8HCID 68511467HCID 68511467, compound

Product 1

HCID 86646931HCID 86646931, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

add 728 mg of dimethyl[(Z)-(methylsulphanyl)methylylidene]biscarbamate to a solution of 1 g of 4-[(2,6-dichlorobenzyl)oxy]benzene-1,2-diamine in a mixture of 60 cm3 of methanol and 212 mg of glacial acetic acid. The mixture is refluxed for 5.5 hours then concentrated under reduced pressure (0.2 kPa). The residue is taken up in 80 cm3 of a saturated aqueous solution in sodium hydrogen carbonate and the mixture obtained is extracted five times with 150 cm3 of ethyl acetate. The combined organic phases are dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue is taken up in 25 cm3 of acetonitrile, washed twice with 5 cm3 of acetonitrile, then dried under reduced pressure over sodium hydroxide. We obtain 834 mg of methyl {6-[(2,6-dichlorobenzyl)oxy]-1H-benzimidazol-2-yl}carbamate in the form of a white powder, which has the following characteristics:

Workup

  1. temperatureThe mixture is refluxed for 5.5 hours
  2. concentrationthen concentrated under reduced pressure (0.2 kPa)
  3. customthe mixture obtained
  4. extractionis extracted five times with 150 cm3 of ethyl acetate
  5. dry with materialThe combined organic phases are dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. washwashed twice with 5 cm3 of acetonitrile
  9. dry with materialdried under reduced pressure over sodium hydroxide

Sources & evidence

ORD record
ord-66d995a0ac7946028860f929da99793d
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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