Hydrochloric Acid → HCID 87307140, compound

HRID 547559Notes

Reaction equation

HRID 547559 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=O)[CH3:2].C(=O)(O)O.[NH2:17][NH:18][C:19]([NH2:21])=[NH:20].[ClH:22]>CO.CCOC(C)=O>[ClH:22].[NH2:20][C:19]([NH2:21])=[N:18]/[N:17]=[C:1](/[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)\[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 114704-Acetylbenzoic AcidHCID 178513185HCID 178513185, compound

Product 1

HCID 87307140HCID 87307140, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

4-Acetylbenzoic acid (L1) (1.041 g, 6.34 mmol), amino guanidine bicarbonate (1.12 g, 8.2 mmol, 1.3 eq) and c.HCl (0.7 ml, 7.0 mmol) in MeOH (30 mL) was refluxed for 1 h. The reaction mixture was diluted with EtOAc cooled to 20° C. and the resulting precipitate was filtered and recrytallized from MeOH/EtOAc to give L2 (887 mg, 55%), mp (MeOH/EtOAc)>300° C.; 1H NMR ([(CD3)2SO] δ7.97-7.89 (m, 4 H, ArH), 6.75 (br, 4 H, 2×NH2), 2.25 (s, 3 H, CH3), mass APCI+ 221.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customto give L2 (887 mg, 55%), mp (MeOH/EtOAc)>300° C.

Sources & evidence

ORD record
ord-e427d33225a243589546ac43ff49d5ff
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

Loading…