Methanol → HCID 19016828, compound

HRID 1728939Notes

Reaction equation

HRID 1728939 reaction equation
[C:1]([C:4]1[S:27][C:7]2[S:8](=[O:26])(=[O:25])[CH2:9][CH2:10][C:11]3[C:12](=[N:13][N:14]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[C:15](=[O:17])[CH:16]=3)[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].CO.C(Cl)(Cl)Cl.[BH4-].[Na+]>O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([N:14]2[C:15](=[O:17])[CH:16]=[C:11]3[CH2:10][CH2:9][S:8](=[O:26])(=[O:25])[C:7]4[S:27][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][C:6]=4[C:12]3=[N:13]2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 10550087HCID 10550087, compound

Product 1

HCID 19016828HCID 19016828, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.5 g of 9-acetyl-2-(4-chlorophenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one 7,7-dioxide obtained in Example 48 in a mixed solvent of 40 ml of methanol and 30 ml of chloroform is added 0.1 g of sodium borohydride under ice-cooling and the mixture is stirred for 30 minutes at room temperature. After the completion of reaction, to the mixture is added water and the solution is extracted with chloroform. The extract is washed with water, dried and concentrated under reduced pressure. The resulting crystals are recrystallized with ethanol to give 0.25 g of 2-(4-chlorophenyl)-9-(1-hydroxyethyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one 7,7-dioxide as white crystals, melting at 233°-235° C.

Workup

  1. temperaturecooling
  2. customAfter the completion of reaction
  3. extractionthe solution is extracted with chloroform
  4. washThe extract is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crystals are recrystallized with ethanol

Sources & evidence

ORD record
ord-6b13c1f80a5b4ea3a5a81b833e594eb3
Source dataset
uspto-grants-1994_07
Patent number
US05329016

Reaction notes

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