Triethylamine → HCID 19082718, compound

HRID 963769Notes

Reaction equation

HRID 963769 reaction equation
[O:1]=[C:2]([Cl:8])[O:3][C:4](Cl)(Cl)Cl.[Cl:9][CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])CO.CCN(CC)CC>C1COCC1>[Cl:9][CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])[CH2:4][O:3][C:2]([Cl:8])=[O:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 19082696HCID 19082696, compound

Product 1

HCID 19082718HCID 19082718, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diphosgene (1.7 ml, 14 mmol) in THF (10 ml, dist. over CaH2) was cooled by means of an ice bath to about 0° C. A solution of 2-chloro-2-(2-nitrophenyl)ethanol (705 mg, 3.5 mmol) and Et3N (354 mg, 0.485 ml, 3.5 mmol) in THF (10 ml, dist. over CaH2) was dropped thereto for about 30 min. After the solution had been stirred for a further hour, the ice bath was removed. The mixture was stirred for another 3 h at room temperature. The mixture was filtered over Celite. The precipitate was rewashed with THF (10 ml, dist. over CaH2). The combined filtrates were concentrated under reduced pressure and then dried in a high vacuum at room temperature. 2-chloro-2-(2-nitrophenyl)ethoxycarbonyl chloride (896 mg, 97%) was obtained as a light brown oil.

Workup

  1. customthe ice bath was removed
  2. stirringThe mixture was stirred for another 3 h at room temperature
  3. filtrationThe mixture was filtered over Celite
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. customdried in a high vacuum at room temperature

Sources & evidence

ORD record
ord-394dd55511b242229200ec5f0e149496
Source dataset
uspto-grants-1998_06
Patent number
US05763599

Reaction notes

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