Acetic Acid → HCID 178470774, compound

HRID 412688Notes

Reaction equation

HRID 412688 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH2:11])[C:5]([OH:7])=[O:6].C(O[C:15](=N)[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])C.C(O)(=O)C>C(OCC)C>[CH2:20]([O:19][C:17]([CH2:16][C:15]1[NH:11][C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[N:1]=1)=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 692633,4-Diaminobenzoic acidHCID 75346Propanoic acid, 3-ethoxy-3-imino-, ethyl ester

Product 1

HCID 178470774HCID 178470774, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3,4-diaminobenzoic acid (9.4 g, 62 mmol), ethyl 3-ethoxy-3-iminopropionate and glacial acetic acid (15 mL) was stirred 30 minutes at 110° C. under nitrogen. The mixture was poured over crushed ice (50 mL) and stirred 30 minutes to give a dark yellow oil. The mixture was stirred while diethyl ether (25 mL) was added to give a gray precipitate. The precipitate was isolated by filtration, washed several times with diethyl ether and dried under vacuum to provide 2-ethoxycarbonylmethyl-1H-benzoimidazole-5-carboxylic acid (12.6 g, 83% yield); 1H-NMR (300 Mhz, DMSO-d6): 12.77 (broad s, 1H), 8.10 (s, 1H), 7.79 (d, 1H, J=8.4 Hz), 7.57 (d, 1H, J=8.4 Hz), 4.11 (q, 2H, J=7.1 Hz), 4.02 (s, 2H), 1.17 (t, 3H, J=7.1 Hz).

Workup

  1. additionThe mixture was poured
  2. stirringstirred 30 minutes
  3. customto give a dark yellow oil
  4. additionwas added
  5. customto give a gray precipitate
  6. customThe precipitate was isolated by filtration
  7. washwashed several times with diethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-4f08f6f283244603b9aec65eecadcd3b
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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