Phosphorus pentachloride → HCID 19076174, compound

HRID 965278Notes

Reaction equation

HRID 965278 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.C(COC1C=CC2NC(=O)CCCC=2C=1)(O)=O.Cl[N:25]1[C:31]2[CH:32]=[CH:33][C:34]([C:36]([O:38][CH3:39])=[O:37])=[CH:35][C:30]=2[CH2:29][CH2:28][C:27]([Cl:41])([Cl:40])[C:26]1=[O:42]>C1(C)C(C)=CC=CC=1>[Cl:41][C:27]1([Cl:40])[CH2:28][CH2:29][C:30]2[CH:35]=[C:34]([C:36]([O:38][CH3:39])=[O:37])[CH:33]=[CH:32][C:31]=2[NH:25][C:26]1=[O:42]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 19076187HCID 19076187, compoundHCID 19076190HCID 19076190, compound

Product 1

HCID 19076174HCID 19076174, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
90 °C

Procedure

Phosphorus pentachloride (40.55 g, 194.7 mmol) was added to a mixture of 7-carbomethoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 2 (14.23 g, 64.91 mmol) and xylene (200 mL) and was heated to 90° C. over a period of 15 min. After an additional 35 min at 90° C. the resulting solution was cooled to RT, filtered, concentrated, and saturated Na2CO3 (200 mL, aqueous) was added to the resulting oil. After stirring the mixture for 1.5 h the solid material was filtered and washed with EtOH (×2) then ether (×2) to give a mixture of 3. (LRMS (ES), [M+H] m/z=288) and a small amount of 1,3,3-trichloro-7-carbomethoxy-2,3,4,5-tetrahydro-1-benzazepin-2-one (13.60 g).

Workup

  1. temperatureAfter an additional 35 min at 90° C. the resulting solution was cooled to RT
  2. filtrationfiltered
  3. concentrationconcentrated
  4. additionsaturated Na2CO3 (200 mL, aqueous) was added to the resulting oil
  5. filtrationwas filtered
  6. washwashed with EtOH (×2)
  7. customether (×2) to give
  8. additiona mixture of 3

Sources & evidence

ORD record
ord-2bc930e87d724284a3a8b1a9966d8b7a
Source dataset
uspto-grants-1998_06
Patent number
US05773512

Reaction notes

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