Hydrochloric Acid → methyl 2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylate

HRID 339422Notes

Reaction equation

HRID 339422 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[NH2:14])[C:7]([O:9][CH3:10])=[O:8].N[C:16](N)=[O:17].Cl>O>[O:17]=[C:16]1[NH:3][C:4]2[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=[CH:12][C:13]=2[NH:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1176UreaHCID 18174510Methyl 3,4-diaminobenzoate dihydrochloride

Product 1

HCID 10352553methyl 2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Methyl 3,4-diaminobenzoate dihydrochloride (20 g, 0.08 mol) was mixed with urea (6.54 g, 0.11 mol). Reaction mixture was heated at ˜150° C. for 7 hours. After cooling powder was suspended in water (400 ml) and pH of the last one was adjusted to 0.45 with hydrochloric acid. Precipitate was filtered and rinsed with water and hydrochloric acid (pH=1.5). Obtained filter cake was dried at ˜100° C. Yield 15.7 g (97%).

Workup

  1. customReaction mixture
  2. temperatureAfter cooling powder
  3. filtrationPrecipitate was filtered
  4. washrinsed with water and hydrochloric acid (pH=1.5)
  5. customObtained
  6. filtrationfilter cake
  7. customwas dried at ˜100° C

Sources & evidence

ORD record
ord-3cda27c755b444d6a916506d13090675
Source dataset
uspto-grants-2014_11
Patent number
US08895118B2

Reaction notes

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