Ammonia → HCID 20184552, compound

HRID 2309907Notes

Reaction equation

HRID 2309907 reaction equation
N[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.N([O-])=[O:25].[Na+].N>C(O)(=O)C.O>[OH:25][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:17])=[O:18])=[CH:11][C:10]=3[O:20][CH3:21])[NH:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 20184521HCID 20184521, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20184552HCID 20184552, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

An amount of 3.2 (9.6 mmol) of 5-amino-2-(2'-methoxy-4'-methanesulfonyloxy-phenyl)-benzimidazole was dissolved in 509 ml of glacial acetic acid, and then a solution of 1.38 gm (20 mmol) of sodium nitrite in 5.0 ml of water was added dropwise, under stirring. After one hour, the mixture was diluted with 100 ml of water, and the solution was refluxed for 1.5 hours. Subsequent to cooling, the solution was adjusted to a pH of 5 with concentrated ammonia and extracted three times, each time with 40 ml of methyl ethyl ketone, and the extracts are dried and concentrated by evaporation in vacuo. The oily residue was chromatographed over 500 gm of aluminium oxide (neutral) (eluant: methylene chloride with 8% ethanol).

Workup

  1. temperaturethe solution was refluxed for 1.5 hours
  2. temperatureSubsequent to cooling
  3. extractionextracted three times
  4. dry with materialeach time with 40 ml of methyl ethyl ketone, and the extracts are dried
  5. concentrationconcentrated by evaporation in vacuo
  6. customThe oily residue was chromatographed over 500 gm of aluminium oxide (neutral) (eluant: methylene chloride with 8% ethanol)

Sources & evidence

ORD record
ord-e4646a5dfaa24a84839f13b93ac13ab1
Source dataset
uspto-grants-1987_09
Patent number
US04696931

Reaction notes

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