Hydrochloric Acid → HCID 59497397, compound

HRID 1747428Notes

Reaction equation

HRID 1747428 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17].Cl.O.C1C[O:24][CH2:23]C1>>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][C:23]1=[O:24]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 13114778Methyl 2-(2-aminoanilino)benzoate

Product 1

HCID 59497397HCID 59497397, compoundYield 78%

Procedure

To a solution of 2-(2-Amino-phenylamino)-benzoic acid methyl ester (75 mg, 0.31 mmol) in THF (1.0 mL) is added COI (100 mg, 0.62 mmol) at room temperature. The mixture is stirred at the same temperature for 16 hours. Then 3 mL of 1.0 M HCl solution is added along with 20 mL of water. The mixture is extracted with EtOAc (3×30 mL) and the organic layers are combined, dried and concentrated to give crude product. Purification by flash column chromatography affords 65 mg (78%) of 2-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-benzoic acid methyl ester.

Workup

  1. extractionThe mixture is extracted with EtOAc (3×30 mL)
  2. customdried
  3. concentrationconcentrated
  4. customto give crude product
  5. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-6f6ace550de945dbb6471e1f7cfc17f6
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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