Triethylamine → HCID 19972408, compound

HRID 1452285Notes

Reaction equation

HRID 1452285 reaction equation
O[CH2:2][C:3]1[C:12]2[O:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:9]([CH3:19])[C:8](=[O:20])[C:7]=2[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.S(Cl)([Cl:30])=O>C(Cl)(Cl)Cl.O>[Cl:30][CH2:2][C:3]1[C:12]2[O:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:9]([CH3:19])[C:8](=[O:20])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 19972525HCID 19972525, compound

Product 1

HCID 19972408HCID 19972408, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

53.4 g of Intermediate II and 38.8 ml of anhydrous triethylamine were dissolved in 440 ml of chloroform. Into this solution, maintained at -10° to -2° C., there was dropped a solution of 19.8 ml of thionyl chloride in 80 ml of anhydrous chloroform. The reaction mixture was stirred at room temperature for 4 hours, and then diluted with 400 ml of water. The aqueous phase was extracted with chloroform, and the extracts were added to the chloroform phase. The chloroform solution was washed with brine, dried on anhydrous sodium sulfate and evaporated to dryness in vacuo. Yield: 56 g of the title compound, which on recrystallization from ethanol was shown to have a melting point of 112°-113° C.

Workup

  1. temperatureInto this solution, maintained at -10° to -2° C.
  2. extractionThe aqueous phase was extracted with chloroform
  3. additionthe extracts were added to the chloroform phase
  4. washThe chloroform solution was washed with brine
  5. dry with materialdried on anhydrous sodium sulfate
  6. customevaporated to dryness in vacuo
  7. customYield: 56 g of the title compound, which on recrystallization from ethanol

Sources & evidence

ORD record
ord-2dba906ae40f469d8876f10e546eef83
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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