Hydrochloric Acid → HCID 67970680, compound

HRID 889538Notes

Reaction equation

HRID 889538 reaction equation
C(OC([NH:8][CH2:9][C:10]1[C:11]([Cl:24])=[C:12]([CH:21]=[CH:22][CH:23]=1)[C:13]([NH:15][C:16]1[NH:17][CH:18]=[CH:19][N:20]=1)=[O:14])=O)(C)(C)C.[ClH:25]>CCOC(C)=O>[ClH:24].[ClH:25].[NH2:8][CH2:9][C:10]1[CH:23]=[CH:22][C:21]([Cl:25])=[C:12]([CH:11]=1)[C:13]([NH:15][C:16]1[NH:17][CH:18]=[CH:19][N:20]=1)=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86667135HCID 86667135, compound

Product 1

HCID 67970680HCID 67970680, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 5-[(tert-butoxycarbonylaminomethyl)-2-chloro-N-(1H-imidazol-2-yl)benzamide (640 mg, 1.82 mmol, 1.0 equiv) in hydrochloric acid (4 M in dioxane, 4.56 mL, 18.24 mmol, 10.0 equiv) and stir at room temperature for 1 h. Pour the reaction mixture into vigorously swirling EtOAc (50 mL), isolate the resulting white precipitate by filtration, wash with EtOAc (25 mL), and dry in a 40° C. vacuum oven overnight to provide the title compound as a white solid (590 mg, 100%). 1H NMR (D2O, 400 MHz) δ 7.53 (d, 1H, J=2.0 Hz), 7.48 (d, 1H, J=8.3 Hz), 7.46 (dd, 1H, J=8.3, 2.0 Hz), 7.04 (s, 2H), 4.05 (s, 2H).

Workup

  1. customisolate the resulting white precipitate
  2. filtrationby filtration
  3. washwash with EtOAc (25 mL)
  4. customdry in a 40° C. vacuum oven overnight

Sources & evidence

ORD record
ord-b19e80b7e5e647e0a2ee2f54dec4750e
Source dataset
uspto-grants-2012_08
Patent number
US08252831B2

Reaction notes

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