Acetic Acid → HCID 178432356, compound

HRID 1898344Notes

Reaction equation

HRID 1898344 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23]([O:25]C)=[O:24])=[CH:13][C:12]=2[N:11]=1.[OH-].[Na+].C(O)(=O)C>CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23]([OH:25])=[O:24])=[CH:13][C:12]=2[N:11]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 178496987HCID 178496987, compound

Product 1

HCID 178432356HCID 178432356, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 7-[(2,6-dichlorophenyl)amino]-2-methyl-8H-imidazo[4,5-e][1,3]benzoxazole-4-carboxylate (0.100 g, 0.256 mmol) in MeOH (15 mL), sodium hydroxide (0.052 g, 1.3 mmol) was added. The reaction mass was refluxed for 3 h. Methanol was removed under vacuum. Water was added and reaction mixture was acidified with dilute acetic acid. The reaction mixture was filtered and obtained solid was dried to afford 0.060 g of the desired product. 1HNMR (DMSO-d6): δ 2.62 (s, 3H), 7.37 (m, 1H), 7.60 (d, J=7.8 Hz, 2H), 7.65 (s, 1H), 9.80 (s, 1H), 11.53 (s, 1H), 13.00 (s, 1H).

Workup

  1. temperatureThe reaction mass was refluxed for 3 h
  2. customMethanol was removed under vacuum
  3. additionWater was added
  4. customreaction mixture
  5. filtrationThe reaction mixture was filtered
  6. customobtained solid
  7. customwas dried

Sources & evidence

ORD record
ord-5d5f61b0ba9a435aa8773d23bdd42279
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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