Hydrochloric Acid → HCID 178524474, compound

HRID 1360982Notes

Reaction equation

HRID 1360982 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:21]=[CH:20][C:16]3[NH:17][N:18]=[N:19][C:15]=3[CH:14]=2)=[O:12])=[CH:6][CH:5]=1.CO.[OH-].[Na+].Cl>C1COCC1.O>[NH:17]1[C:16]2[CH:20]=[CH:21][C:13]([C:11]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:22])=[O:2])=[CH:5][CH:6]=3)=[O:12])=[CH:14][C:15]=2[N:19]=[N:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 178498162HCID 178498162, compound

Product 1

HCID 178524474HCID 178524474, compoundYield 8.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[(1H-Benzotriazole-5-carbonyl)amino]benzoic acid methyl ester (5.2 g, 17.6 mmol) was dissolved in THF (60 mL) and methanol (10 mL) was added followed by 1N sodium hydroxide (35 mL). The mixture was stirred at room temperature for 16 hours and then 1N hydrochloric acid (45 mL) was added. The mixture was added water (200 mL) and extracted with ethyl acetate (2×500 mL). The combined organic phases were evaporated in vacuo to afford 0.44 g of 4-[(1H-benzotriazole-5-carbonyl)amino]benzoic acid. By filtration of the aqueous phase a further crop of 4-[(1H-benzotriazole-5-carbonyl)amino]benzoic acid was isolated (0.52 g).

Workup

  1. extractionextracted with ethyl acetate (2×500 mL)
  2. customThe combined organic phases were evaporated in vacuo

Sources & evidence

ORD record
ord-45a006428d6d4d33a5e81780c5957d86
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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