Triethylamine → HCID 86690418, compound

HRID 241239Notes

Reaction equation

HRID 241239 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C:9]2=[O:14])=[CH:4][CH:3]=1.C([N:17]([CH2:20]C)CC)C.ClC([O:26]C(Cl)=O)(Cl)Cl>C(Cl)Cl>[N:17]([C:6]1[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][C:9]1=[O:14])=[C:20]=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 111948544-(4-Aminophenyl)morpholin-3-one

Product 1

HCID 86690418HCID 86690418, compoundYield 307.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under an atmosphere of nitrogen to a suspension of 25.9 g of 4-(4-amino-phenyl)-morpholin-3-one (APMO) (MW=192.22; 1 eq.) and 27.2 g of triethylamine (MW=101.19; 2 eq.) in 390 mL of methylene chloride was added at room temperature a solution of 14.6 g chloroformic acid trichloromethyl ester (MW=197.83; 0.55 eq.) in 390 mL of methylene chloride within 10 minutes. The reaction was slight exothermic and the temperature rose to 35° C. After stirring at room temperature for two hours the resulting suspension was filtered and the filtrate was concentrated in vacuo at 45° C. to afford 49.5 g of the title compound. The resulting material was used in the following step without further purification.

Workup

  1. customrose to 35° C
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated in vacuo at 45° C.

Sources & evidence

ORD record
ord-410e414d50014e25a036b2b4cb64a0fd
Source dataset
uspto-grants-2014_02
Patent number
US08648189B2

Reaction notes

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