Acetic Acid → HCID 178476708, compound

HRID 556735Notes

Reaction equation

HRID 556735 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=[CH:14][CH:15]=O.C(=O)(O)O.[NH2:21][NH:22][C:23]([NH2:25])=[NH:24].[C:26]([OH:29])(=[O:28])[CH3:27]>C(O)C>[C:26]([O-:29])(=[O:28])[CH3:27].[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=[CH:14][CH:15]=[N:21][NH:22][C:23]([NH2:25])=[NH2+:24]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 86652392HCID 86652392, compoundHCID 178513185HCID 178513185, compound

Product 1

HCID 178476708HCID 178476708, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.9 g (3.26 mmol) 4b and 1.2 eqv. of aminoguanidine bicarbonate was mixed in 10 ml of ethanol and 2 ml of acetic acid and refluxed for 30 min. The solvent was evaporated and the oily residue was dissolved in acetonitrile and a few drops of diethyl ether was added. After three days in refrigerator a precipitate was formed that was filtered, washed with diethyl ether and dried. 340 mg (31%) of the final product 5b was obtained as white crystals (m.p. 166-168° C.).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe oily residue was dissolved in acetonitrile
  3. additiona few drops of diethyl ether was added
  4. customAfter three days in refrigerator a precipitate was formed
  5. filtrationthat was filtered
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-296e9030752d4fcbbb67d3f09bf32613
Source dataset
uspto-grants-2011_11
Patent number
US08058306B2

Reaction notes

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