Methanol → 2-Methyl-1-propyl-1,3-benzodiazole-5-carboxylic acid

HRID 74261Notes

Reaction equation

HRID 74261 reaction equation
CO.[NH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][CH2:14][CH2:15][CH3:16])[C:7]([OH:9])=[O:8].Cl.[C:18](=N)(OC)[CH3:19]>C(OCC)C>[CH3:18][C:19]1[N:13]([CH2:14][CH2:15][CH3:16])[C:12]2[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 115864403-Amino-4-(propylamino)benzoic acid

Product 1

HCID 202988562-Methyl-1-propyl-1,3-benzodiazole-5-carboxylic acidYield 116.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a methanol (17 mL) solution of 3-amino-4-n-propylaminobenzoic acid (see Working Example 82-2) (1.68 g, 8.65 mmol) was added methyl acetimidate hydrochloride (1.14 g, 10.4 mmol), and this was heated to reflux for 4 hours. After the reaction was complete, this was cooled to room temperature, diethyl ether was added, and this was allowed to stand at room temperature for 10 minutes. The crystals obtained were filtered, and after being washed with diethyl ether, they were dried to yield the title compound (2.20 g, quant.).

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 4 hours
  3. customThe crystals obtained
  4. filtrationwere filtered
  5. washafter being washed with diethyl ether, they
  6. customwere dried

Sources & evidence

ORD record
ord-3eb052daec9a47e6839ab79527356e8e
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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