Hydrochloric Acid → HCID 1284950, compound

HRID 2233533Notes

Reaction equation

HRID 2233533 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].N[C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1N)[C:9]([OH:11])=[O:10].O.Cl>C(O)CCCC>[N:1]1[C:2](=[O:3])[N:4]=[C:13]2[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[CH:7]=[CH:6][C:14]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1176UreaHCID 692633,4-Diaminobenzoic acid

Product 1

HCID 1284950HCID 1284950, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

Urea (1.20 g, 0.0200 mol) and 3,4-diaminobenzoic acid (3) (3.04 g, 0.0200 mol) in pentan-1-ol (10 mL) was vigorously stirred and heated to reflux under a nitrogen atmosphere. The heating was discontinued after 4 hours and on cooling to room temperature, water (30 mL) was added. The pH was adjusted to 1 with conc. HCl. The resultant dark solid was filtered off, washed with further water (2×20 mL) and dried to give 3.00 g (84% yield) of benzimidazol-2-one-5-carboxylic acid (4) as a black powder,

Workup

  1. temperatureheated
  2. temperatureto reflux under a nitrogen atmosphere
  3. filtrationThe resultant dark solid was filtered off
  4. washwashed with further water (2×20 mL)
  5. customdried

Sources & evidence

ORD record
ord-8509b029741c4a3787bc021cdfb863d9
Source dataset
uspto-grants-2010_05
Patent number
US07709514B2

Reaction notes

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