Water → HCID 20449980, compound

HRID 358040Notes

Reaction equation

HRID 358040 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=O)[CH2:9][CH:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:6]=2[CH:20]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:30]2)=CC=1.O>CN(C)P(=O)(N(C)C)N(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[S:30])[CH2:9][CH:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:6]=2[CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 22105454HCID 22105454, compound

Product 1

HCID 20449980HCID 20449980, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

20.2 g of 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1-benzazepin-2-one are dissolved in 110 ml of hexamethylphosphoric acid triamide and treated with 13.8 g of 2,4-bis-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulphide. The mixture is warmed to 100° for 1 hour, again cooled to room temperature and poured into 2.2 l of water. The mixture is extracted three times with ethyl acetate and the organic extracts are washed with water, sodium hydrogen carbonate solution and with saturated sodium chloride solution. The ethyl acetate solutions are evaporated and the residue is chromatographed on 400 g of silica gel. By elution with toluene and toluene/chloroform (19:1) and recrystallization of the resulting material from diisopropyl ether there is obtained 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1-benzazepine-2-thione of melting point 179°-181°.

Workup

  1. temperatureThe mixture is warmed to 100° for 1 hour
  2. extractionThe mixture is extracted three times with ethyl acetate
  3. washthe organic extracts are washed with water, sodium hydrogen carbonate solution and with saturated sodium chloride solution
  4. customThe ethyl acetate solutions are evaporated
  5. customthe residue is chromatographed on 400 g of silica gel
  6. washBy elution
  7. customwith toluene and toluene/chloroform (19:1) and recrystallization of the resulting material from diisopropyl ether

Sources & evidence

ORD record
ord-36b027200d36482bbdff2d6a6491b719
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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