Triethylamine → HCID 85991107, compound

HRID 2095235Notes

Reaction equation

HRID 2095235 reaction equation
[Cl:1][C:2]([O:4][C:5](Cl)(Cl)Cl)=[O:3].[C:9]([C:17]1[CH:18]=[CH:19][C:20]([N+:27]([O-:29])=[O:28])=[C:21]([CH:23](C)[CH2:24]O)[CH:22]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>O1CCCC1>[C:9]([C:17]1[CH:18]=[CH:19][C:20]([N+:27]([O-:29])=[O:28])=[C:21]([CH:23]([CH3:24])[CH2:5][O:4][C:2]([Cl:1])=[O:3])[CH:22]=1)(=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 59386296[3-(2-Hydroxy-1-methylethyl)-4-nitrophenyl]phenylmethanone

Product 1

HCID 85991107HCID 85991107, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of trichloromethyl chloroformate (15.83 g, 80 mmol, 0.8 equivalents) in dry tetrahydrofuran (150 mL), which has been pre-cooled to 0° C., was added over a period of approximately 2 hours a solution of 2-(5-benzoyl-2-nitrophenyl)-1-propanol (41) (28.53 g, 100 mmol) and triethylamine (10.12 g, 100 mmol) in tetrahydrofuran (250 mL) with continued cooling. After stirring for 1 hour at ambient temperature the resulting suspension was filtered, the filter cake was washed with a little tetrahydrofuran, and the combined organic phases were concentrated in vacuo to give 19f as yellow oil.

Workup

  1. filtrationwas filtered
  2. washthe filter cake was washed with a little tetrahydrofuran
  3. concentrationthe combined organic phases were concentrated in vacuo

Sources & evidence

ORD record
ord-2472b863a3504d998b70f0556882ccd2
Source dataset
uspto-grants-2013_05
Patent number
US08445734B2

Reaction notes

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