Water → HCID 22908984, compound

HRID 1378978Notes

Reaction equation

HRID 1378978 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:31](O)(=[O:33])=[O:32])[C:6](=[CH:27][C:28]=1[O:29][CH3:30])/[CH:7]=[CH:8]/[C:9]1[N:17]([CH3:18])[C:16]2[C:15](=[O:19])[N:14]([CH2:20][CH2:21][CH3:22])[C:13](=[O:23])[N:12]([CH2:24][CH2:25][CH3:26])[C:11]=2[N:10]=1.S(Cl)(Cl)=O.[CH2:39]([NH:41][CH2:42][CH3:43])[CH3:40].O>CN(C)C=O>[CH2:39]([N:41]([CH2:42][CH3:43])[S:31]([C:5]1[C:6](=[CH:27][C:28]([O:29][CH3:30])=[C:3]([O:2][CH3:1])[CH:4]=1)/[CH:7]=[CH:8]/[C:9]1[N:17]([CH3:18])[C:16]2[C:15](=[O:19])[N:14]([CH2:20][CH2:21][CH3:22])[C:13](=[O:23])[N:12]([CH2:24][CH2:25][CH3:26])[C:11]=2[N:10]=1)(=[O:32])=[O:33])[CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 22909004HCID 22909004, compound

Product 1

HCID 22908984HCID 22908984, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 1 (1.00 g, 1.96 mmol) obtained in Example 1 was dissolved in 20 ml of dimethylformamide. To the solution was dropwise added 0.29 ml (3.92 mmol) of thionyl chloride under ice-cooling, and the resulting mixture was stirred at room temperature for 10 minutes. After ice-cooling, 1.02 ml (9.80 mmol) of diethylamine was added dropwise to the mixture, and the resulting mixture was stirred at room temperature for one hour. The mixture was poured into 50 ml of water and extracted three times with 20 ml of chloroform. The extract was washed successively with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was purified by column chromatography (eluent: 65% ethyl acetate/hexane), followed by recrystallization from cyclohexane/toluene to give 320 mg (yield 30%) of Compound 2 as a pale yellow powder.

Workup

  1. temperaturecooling
  2. temperatureAfter ice-cooling
  3. stirringthe resulting mixture was stirred at room temperature for one hour
  4. extractionextracted three times with 20 ml of chloroform
  5. washThe extract was washed successively with water
  6. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  7. customfollowed by evaporation under reduced pressure
  8. customThe residue was purified by column chromatography (eluent: 65% ethyl acetate/hexane)
  9. customfollowed by recrystallization from cyclohexane/toluene

Sources & evidence

ORD record
ord-8b20f65acdf745148e73e0d98b6f82d8
Source dataset
uspto-grants-1997_09
Patent number
US05670498

Reaction notes

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