3-Amino-4-(propylamino)benzoic acid → 2-Methyl-1-propyl-1,3-benzodiazole-5-carboxylic acid

HRID 1448088Notes

Reaction equation

HRID 1448088 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][CH2:12][CH2:13][CH3:14])[C:5]([OH:7])=[O:6].Cl.[CH2:16](C(=N)OCC)[CH3:17]>C(O)(=O)C>[CH3:16][C:17]1[N:11]([CH2:12][CH2:13][CH3:14])[C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 115864403-Amino-4-(propylamino)benzoic acidHCID 13000588Ethyl propanecarboximidate hydrochloride

Product 1

HCID 202988562-Methyl-1-propyl-1,3-benzodiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4.5 parts of 3-amino-4-(propylamino)benzoic acid, 2.6 parts of ethyl ethanecarboximidate hydrochloride and 50 parts of acetic acid is stirred first for 20 minutes at room temperature and further for 10 minutes at reflux. The reaction mixture is evaporated. The residue is crystallized from 2-propanol. The product is filtered off, washed with water and 2-propanol and dried, yielding 1.8 parts of 2-methyl-1-propyl-1H-benzimidazole-5-carboxylic acid; mp. >260° C.

Workup

  1. temperatureat reflux
  2. customThe reaction mixture is evaporated
  3. customThe residue is crystallized from 2-propanol
  4. filtrationThe product is filtered off
  5. washwashed with water and 2-propanol
  6. customdried

Sources & evidence

ORD record
ord-a5d7690b7d704eac937afc9326c9fb9b
Source dataset
uspto-grants-1979_12
Patent number
US04179505

Reaction notes

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