Diisopropylcarbodiimide → 2-(2,6-Dichloro-phenylamino)-6-fluoro-1-methyl-1h-benzimidazole-5-carboxylic acid

HRID 1406484Notes

Reaction equation

HRID 1406484 reaction equation
CC(C)N=C=NC(C)C.C([O:12][C:13](=[O:35])[C:14]1[CH:19]=[C:18]([NH:20][C:21]([NH:23][C:24]2[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:31])=S)[C:17]([NH:32][CH3:33])=[CH:16][C:15]=1[F:34])C>C(#N)C>[Cl:30][C:29]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:31])[C:24]=1[NH:23][C:21]1[N:32]([CH3:33])[C:17]2[CH:16]=[C:15]([F:34])[C:14]([C:13]([OH:12])=[O:35])=[CH:19][C:18]=2[N:20]=1

Participants

4

Reactant 2

HCID 12734DiisopropylcarbodiimideHCID 86660379Ethyl 5-(3-(2,6-dichlorophenyl)thioureido)-2-fluoro-4-(methylamino)benzoate

Product 1

HCID 672306452-(2,6-Dichloro-phenylamino)-6-fluoro-1-methyl-1h-benzimidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

DIC (1.50 mL, 9.6 mmol) was added to a stirred mixture of 5-[3-(2,6-dichloro-phenyl)-thioureido]-2-fluoro-4-methylamino-benzoic acid ethyl ester (2.70 g, 6.5 mmol) in acetonitrile. After stirring for 1 h the mixture was concentrated i.vac. The residue was taken up in ethanol and 1 M aq. NaOH and stirred for further 40 min at reflux. Ethanol was evaporated, the mixture was diluted with water and filtered. The filtrate was acidified with hydrochloric acid, stirred and filtered. Both residues were combined and dried.

Workup

  1. concentrationwas concentrated i.vac
  2. stirring1 M aq. NaOH and stirred for further 40 min
  3. temperatureat reflux
  4. customEthanol was evaporated
  5. additionthe mixture was diluted with water
  6. filtrationfiltered
  7. stirringstirred
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-6c3b82e7176746e5a2539763006d63e1
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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