Triethylamine → HCID 19972408, compound

HRID 2400166Notes

Reaction equation

HRID 2400166 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×

Conditions

Temperature
-2 °C

Procedure

53.4 g of Intermediate II and 38.8 ml of anhydrous triethylamine were dissolved in 440 ml of chloroform. A solution of 19.8 ml of thionyl chloride in 80 ml of anhydrous chloroform was added to the above solution, which was maintained at -10°/-2° C. The reaction mixture was stirred at ambient 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 sulphate and evaporated to dryness in vacuo. Yield: 56 g of the title compound, which, recrystallized from ethanol, has a melting point of 112°-113° C.

Workup

  1. extractionThe aqueous phase was extracted with chloroform
  2. additionthe extracts were added to the chloroform phase
  3. washThe chloroform solution was washed with brine
  4. dry with materialdried on anhydrous sodium sulphate
  5. customevaporated to dryness in vacuo
  6. customYield: 56 g of the title compound, which, recrystallized from ethanol

Sources & evidence

ORD record
ord-9547ec1c253b44c490ece97fba9a43be
Source dataset
uspto-grants-1995_09
Patent number
US05453518

Reaction notes

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