Formic Acid → 6-[1-(2-Acetylaminoethyl)benzimidazol-5-yl]-3(2H)-pyridazinone

HRID 846094Notes

Reaction equation

HRID 846094 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:15]2[CH:16]=[CH:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13].[CH:22](O)=O>>[C:12]([NH:11][CH2:10][CH2:9][N:8]1[C:7]2[CH:6]=[CH:5][C:4]([C:15]3[CH:16]=[CH:17][C:18](=[O:21])[NH:19][N:20]=3)=[CH:3][C:2]=2[N:1]=[CH:22]1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 151078126-(3-amino-4-acetylaminoethylaminophenyl)-3(2H)-pyridazinone

Product 1

HCID 148843956-[1-(2-Acetylaminoethyl)benzimidazol-5-yl]-3(2H)-pyridazinone

Procedure

14.2 g (49.4 mmol) of 6-(3-amino-4-acetylaminoethylaminophenyl)-3(2H)-pyridazinone are refluxed for one hour in 60 ml of formic acid. Then the excess formic acid is distilled off in vacuo, the residue is mixed with 50 ml of ice water and then adjusted to pH 8-9 with concentrated ammonia solution. The product precipitated is suction filtered, washed with about 50 ml of cold water, then with 50 ml of ether and dried.

Workup

  1. distillationThen the excess formic acid is distilled off in vacuo
  2. additionthe residue is mixed with 50 ml of ice water
  3. customThe product precipitated
  4. filtrationfiltered
  5. washwashed with about 50 ml of cold water
  6. dry with materialwith 50 ml of ether and dried

Sources & evidence

ORD record
ord-7cf75357effb4f2d9625664729f0780f
Source dataset
uspto-grants-1992_08
Patent number
US05135932

Reaction notes

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