Triethylamine → HCID 58346342, compound

HRID 1941770Notes

Reaction equation

HRID 1941770 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]2[O:14][CH2:15][C:16]([CH3:18])([CH3:17])[N:7]3[C:8]=2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([NH2:21])=O)=[CH:6]3.C(N(CC)CC)C.O=P(Cl)(Cl)Cl>C(Cl)Cl>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]2[O:14][CH2:15][C:16]([CH3:18])([CH3:17])[N:7]3[C:8]=2[C:3]=1[C:4](=[O:22])[C:5]([C:19]#[N:21])=[CH:6]3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 58346343HCID 58346343, compound

Product 1

HCID 58346342HCID 58346342, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 11 (2.92 g, 9.44 mmol) and triethylamine (6.6 mL, 47 mmol) in CH2Cl2 (20 ml) was cooled to 0° C. and POCl3 (4.35 g, 28 mmol) was added drop wise with stirring. The mixture was stirred an additional 5 h at 0° C. During that time, the reaction mixture turned dark-brown. Upon completion of the reaction, the solvent was removed by evaporation. 70 mL of water were added and the mixture stirred at room temperature for 1 h. The precipitate that formed was collected by filtration and washed with water. The solid was dried under vacuum to yield 12 as a brown solid (2.6 g, 94%). This compound was used without further purification in the next step.

Workup

  1. stirringThe mixture was stirred an additional 5 h at 0° C
  2. customUpon completion of the reaction
  3. customthe solvent was removed by evaporation
  4. addition70 mL of water were added
  5. stirringthe mixture stirred at room temperature for 1 h
  6. customThe precipitate that formed
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-db3c4026d04945afadba676a539ffe9b
Source dataset
uspto-grants-2013_03
Patent number
US08389514B2

Reaction notes

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