Phosgene → HCID 21072848, compound

HRID 1372900Notes

Reaction equation

HRID 1372900 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:11]=CC=C[C:7]=1C(O)(C)C.N[CH2:17][C:18](C1C=CC=CC=1)=O.C[Mg]I.[CH2:29]1[CH2:33][O:32][CH2:31][CH2:30]1>>[CH3:7][C:6]1([CH3:11])[C:30]2[CH:29]=[CH:33][CH:17]=[CH:18][C:31]=2[O:32][C:1](=[O:2])[NH:5]1

Participants

6

Reactant 5

HCID 6371PhosgeneHCID 8028Tetrahydrofuran2×HCID 11952PhenacylamineHCID 2535272-(2-aminophenyl)propan-2-olHCID 178418373HCID 178418373, compound

Product 1

HCID 21072848HCID 21072848, compound

Procedure

112 g (1.13 mol) phosgene are piped into 500 mL THF. Then a solution of 52 g (0.34 mol) 2-(2-amino-phenyl)-propan-2-ol, prepared from 2-aminoacetophenone and methylmagnesium iodide, in 300 mL THF is added. The reaction mixture is left to stand overnight, evaporated down and combined with 500 ml pyridine. After the pyridine has been distilled off water is added and the mixture is extracted with diethyl ether. The organic phases are washed successively with 2 N hydrochloric acid, sodium hydroxide solution and water, dried with sodium sulphate and evaporated down. The residue remaining (46 g) is further reacted directly without any more purification.

Workup

  1. additionis added
  2. waitThe reaction mixture is left
  3. customevaporated down
  4. distillationAfter the pyridine has been distilled off water
  5. additionis added
  6. extractionthe mixture is extracted with diethyl ether
  7. washThe organic phases are washed successively with 2 N hydrochloric acid, sodium hydroxide solution and water
  8. dry with materialdried with sodium sulphate
  9. customevaporated down
  10. customis further reacted directly without any more purification

Sources & evidence

ORD record
ord-dae4c0f8100449db99fdd854c66b7f30
Source dataset
uspto-grants-2007_01
Patent number
US07160882B2

Reaction notes

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