Acetic Acid → HCID 20184537, compound

HRID 1380765Notes

Reaction equation

HRID 1380765 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][C:10]=3[O:20][CH3:21])[NH:8][C:4]=2[CH:3]=1.[O-:24][C:25]#[N:26].[K+].C(O)(=O)C>O1CCCC1>[NH2:26][C:25]([NH:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][C:10]=3[O:20][CH3:21])[NH:8][C:4]=2[CH:3]=1)=[O:24]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 20184521HCID 20184521, compound

Product 1

HCID 20184537HCID 20184537, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

One gram (3.0 mmol) of 5-amino-2-(2'-methoxy-4'-methanesulfonyloxy-phenyl)-benzimidazole were dissolved in 20 ml of pure tetrahydrofuran, and then 2.0 gm of potassium cyanate and 5 ml of 2M acetic acid were added successively. After the mixture refluxed for eight hours, the solvent was evaporated off in vacuo, and the residue was mixed with 10 ml of water and neutralized with 5% sodium bicarbonate solution. The crude product precipitated was subjected to suction filtration and chromatographed over 200 gm of silica gel (eluant: methylene chloride with 8% ethanol).

Workup

  1. temperatureAfter the mixture refluxed for eight hours
  2. customthe solvent was evaporated off in vacuo
  3. additionthe residue was mixed with 10 ml of water and neutralized with 5% sodium bicarbonate solution
  4. customThe crude product precipitated
  5. filtrationwas subjected to suction filtration
  6. customchromatographed over 200 gm of silica gel (eluant: methylene chloride with 8% ethanol)

Sources & evidence

ORD record
ord-a7e7c6ee94a94560bceee761005ddb98
Source dataset
uspto-grants-1986_04
Patent number
US04582837

Reaction notes

Loading…