Chloroform → 8-Fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]-thiepin-10-ol

HRID 372171Notes

Reaction equation

HRID 372171 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH2:8][C@@H:7](N3CCN(CCN4CCOC4=O)CC3)[C:6]=2[CH:31]=1.C(Cl)(Cl)Cl.CS(O)(=O)=[O:38]>C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH2:8][CH:7]([OH:38])[C:6]=2[CH:31]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6395Methanesulfonic AcidHCID 3042546(-)-(R)-3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]ethyl}-2-oxazolidinone

Product 1

HCID 122755428-Fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]-thiepin-10-olYield 97%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5.0 G. of enriched (-)-(R)-3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]ethyl}-2-oxazolidinone αD20 = -9.5°; α365 = +125.0° (chloroform; c = 2.50%)] are heated under reflux for 18 hours with stirring in 81 ml. of 0.5-M methanesulfonic acid and the mixture is subsequently treated with benzene. The organic phase is washed with water, dried over sodium sulfate and evaporated. The residue is crystallized from n-hexane, and there is obtained racemic 8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-ol having a melting point of 89.5°-90° C. The yield is 97%. This compound can be converted in accordance with the procedure described in Example 1 into the 10-chloro compound which can subsequently be used in Example 1 or 11.

Workup

  1. temperatureunder reflux for 18 hours
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue is crystallized from n-hexane

Sources & evidence

ORD record
ord-ccd105e6af9c45e69f09d69770d6bd4f
Source dataset
uspto-grants-1978_05
Patent number
US04089861

Reaction notes

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