Dichloromethane → HCID 23371588, compound

HRID 1757394Notes

Reaction equation

HRID 1757394 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:12][N+:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH2:24][S:23][C:22](=[O:25])[NH:21][N:20]=3)=[CH:15][CH:14]=2)=[O:11])=[CH:6][CH:5]=1.[BH4-].[Na+].ClCCl>CO>[OH:11][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:9][CH:8]=1)[CH2:12][N:13]1[CH2:18][CH2:17][C:16]([C:19]2[CH2:24][S:23][C:22](=[O:25])[NH:21][N:20]=2)=[CH:15][CH2:14]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 23371593HCID 23371593, compound

Product 1

HCID 23371588HCID 23371588, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[(4-Methoxyphenyl)carbonylmethyl]-4-(3H,6H-1,3,4-thiadiazin-2-one-5-yl)pyridinium bromide (760 mg, 1.8 mmol) was dissolved in methanol (8 ml) and gradually added with sodium borohydride (680 mg, 18 mmol) under ice-cooling and then stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue obtained was added with dichloromethane, washed with water and dried over anhydrous magnesium sulfate. The residue obtained by evaporation was purified by column chromatography (dichloromethane-methanol=20:1) to obtain the titled compound (423 mg) as white crystals.

Workup

  1. temperaturecooling
  2. customThe solvent was removed under reduced pressure
  3. customThe residue obtained
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe residue obtained by evaporation
  7. customwas purified by column chromatography (dichloromethane-methanol=20:1)

Sources & evidence

ORD record
ord-6f0d4dcefbf142389af733e9445db092
Source dataset
uspto-grants-1995_08
Patent number
US05446042

Reaction notes

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