Hydrochloric Acid → HCID 20156394, compound

HRID 986772Notes

Reaction equation

HRID 986772 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[C:10]1[N:11]=[C:12]2[N:17]([CH:18]=1)[N:16]=[CH:15][N:14]=[CH:13]2.[CH3:19][S:20](Cl)(=[O:22])=[O:21].Cl>[OH-].[Na+].C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][S:20]([CH3:19])(=[O:22])=[O:21])[CH:6]=[CH:5][C:4]=1[C:10]1[N:11]=[C:12]2[N:17]([CH:18]=1)[N:16]=[CH:15][N:14]=[CH:13]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 20156400HCID 20156400, compound

Product 1

HCID 20156394HCID 20156394, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

55 mg (0.227 mmol) of 6-(2-Methoxy-4-hydroxyphenyl)-imidazo[2,1-f][1,2,4]triazine are dissolved in 12 ml of 1N sodium hydroxide solution. 0.2 ml of methanesulphonic acid chloride are added to the clear yellowish-orange solution and the resulting mixture is stirred for 21/2 hours at ambient temperature. The reaction solution is then adjusted to pH 6 with 1N hydrochloric acid and extracted three times, each time with 25 ml of ethyl acetate. The ethyl acetate phase is dried over sodium sulphate and concentrated by evaporation. The residue obtained is dissolved in methylene chloride and applied to a silica gel column, eluting first with methylene chloride and later with methylene chloride/ethanol (50:1). The desired eluates are concentrated by evaporation, then triturated with ether/petroleum ether (1:1) and the crystals obtained are suction filtered.

Workup

  1. extractionextracted three times
  2. dry with materialThe ethyl acetate phase is dried over sodium sulphate
  3. concentrationconcentrated by evaporation
  4. customThe residue obtained
  5. washeluting first with methylene chloride and later with methylene chloride/ethanol (50:1)
  6. concentrationThe desired eluates are concentrated by evaporation
  7. customtriturated with ether/petroleum ether (1:1)
  8. customthe crystals obtained

Sources & evidence

ORD record
ord-6345be6a58f249bf9276ae4961a69bc8
Source dataset
uspto-grants-1987_12
Patent number
US04716169

Reaction notes

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