Phosphorus oxide (P4O10) → HCID 15615710, compound

HRID 476543Notes

Reaction equation

HRID 476543 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:21])[CH2:9][CH2:10][NH:11][C:12](=O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[I:19])=[CH:4][CH:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(Cl)(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH3:21])[CH2:9][CH2:10][N:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[I:19])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 15615709HCID 15615709, compound

Product 1

HCID 15615710HCID 15615710, compoundYield 94.7%

Procedure

After a mixture of 181 mg of N'-(4-chlorophenyl)-N-(2-iodobenzoyl)-N'-methylethylenediamine, 925 mg of phosphorus pentoxide and 4 ml of phosphorus oxychloride had been stirred at 115° C. to 120° C. for 4 hours, the reaction mixture was allowed to cool and poured into ice water to decompose an excess of the reagents. After having been washed with ether, the aqueous phase was alkalized with sodium carbonate and then extracted with ethyl acetate. After the organic phase had been washed with water, distilling off the solvent therefrom gave 164 mg of 7-chloro-2,3-dihydro-5-(2-iodophenyl)-1-methyl-1H-1,4-benzodiazepine.

Workup

  1. temperatureto cool
  2. washAfter having been washed with ether
  3. extractionextracted with ethyl acetate
  4. washAfter the organic phase had been washed with water
  5. distillationdistilling off the solvent

Sources & evidence

ORD record
ord-5b67fce45ec84e75ad84af1854be0813
Source dataset
uspto-grants-1989_12
Patent number
US04885152

Reaction notes

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