Thionyl Chloride → HCID 23332599, compound

HRID 224365Notes

Reaction equation

HRID 224365 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=2[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:7][CH:6]([F:22])[CH2:5]1.[O:25]=S(Cl)Cl.[O-][Mn](=O)(=O)=O.[K+].OS([O-])=O.[Na+]>N1C=CC=CC=1.CC(C)=O>[F:24][C:2]([F:1])([F:23])[CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=2[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:7][CH:6]([F:22])[C:5]1=[O:25]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 516875Potassium PermanganateHCID 23332721HCID 23332721, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 23332599HCID 23332599, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1049PyridineSolvent

Procedure

3.57 g. of 1-(2,2,2-trifluoroethyl)-3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepine, obtainable from the corresponding 3-hydroxy compound by reaction with SOCl2 and then AgF, is dissolved in a mixture of 35 ml. of acetone and 20 ml. of pyridine; 1.35 g. of KMnO4 are added in portions. During the addition, the mixture is briefly boiled up after each addition until the violet color has disappeared. The mixture is then heated at 100° for 1 hour more. NaHSO3 solution is added to decompose the excess oxidizing agent and the mixture is worked up in the customary manner to give 1-(2,2,2-trifluoroethyl)-3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one.

Workup

  1. dissolutionAgF, is dissolved in a mixture of 35 ml
  2. additionDuring the addition
  3. additionafter each addition until the violet color
  4. temperatureThe mixture is then heated at 100° for 1 hour more

Sources & evidence

ORD record
ord-3f73d6fdb25b4dd4be2f8322eefa569e
Source dataset
uspto-grants-1980_11
Patent number
US04232016

Reaction notes

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