Methanol → HCID 178498153, compound

HRID 2117299Notes

Reaction equation

HRID 2117299 reaction equation
[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)[C:2]([NH2:4])=[NH:3].S(Cl)(Cl)=O.[CH3:18]O>ClCCl>[CH3:18][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:5]([NH:1][C:2]([NH2:4])=[NH:3])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178512548HCID 178512548, compound

Product 1

HCID 178498153HCID 178498153, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 4-guanidino benzoic acid (20.0 g, 93 mmol) in methanol (600 mL) was added thionyl chloride (12 mL) drop wise. The reaction mixture was stirred at room temperature overnight. The reaction was concentrated in vacuo to give a white powder. The crude material was dissolved in dichloromethane and evaporated to provide the title compound as a white powder (17.95 g, 100% yield): HPLC Retention Time; 1.27 min (Method A). M+1; 193.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto give a white powder
  3. customevaporated

Sources & evidence

ORD record
ord-35b8c5b02fcf4633b3f105adf729771f
Source dataset
uspto-grants-2008_10
Patent number
US07442699B2

Reaction notes

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