Water → HCID 20449993, compound

HRID 358065Notes

Reaction equation

HRID 358065 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:12][C:11](=O)[CH2:10][CH2:9][S:8](=[O:15])(=[O:14])[CH:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:6]=2[CH:23]=1.COC1C=CC([SH:32]2(=S)PP(=S)(C3C=CC(OC)=CC=3)S2)=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:12][C:11](=[S:32])[CH2:10][CH2:9][S:8](=[O:15])(=[O:14])[CH:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 20449977HCID 20449977, compoundHCID 178492777HCID 178492777, compound

Product 1

HCID 20449993HCID 20449993, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 13.4 g of 8-chloro-6-(2-fluorophenyl)-1,3,4,6-tetrahydro-2-oxo-2H-5,1-benzothiazocine 5,5-dioxide in 380 ml of hexamethylphosphoric acid triamide is treated with 7.7 g of 2,4-bis-(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane-2,4-disulphide, the mixture is heated to 100° for 2 hours, again cooled to room temperature and then poured into 8.3 l of water. The mixture is extracted twice with ethyl acetate and the organic extracts are washed with water and with saturated sodium chloride solution. The ethyl acetate solutions are evaporated and the residue is chromatographed on 500 g of silica gel. By elution with chloroform which contains 0.5% ethanol and crystallization from ether there is obtained 8-chloro-6-(2-fluorophenyl)-1,3,4,6-tetrahydro-2-thiono-2H-5,1-benzothiazocine 5,5-dioxide of melting point 226°.

Workup

  1. temperaturethe mixture is heated to 100° for 2 hours
  2. extractionThe mixture is extracted twice with ethyl acetate
  3. washthe organic extracts are washed with water and with saturated sodium chloride solution
  4. customThe ethyl acetate solutions are evaporated
  5. customthe residue is chromatographed on 500 g of silica gel
  6. washBy elution with chloroform which
  7. custom0.5% ethanol and crystallization from ether

Sources & evidence

ORD record
ord-cce5ee40002f4d37ab1c1c5dc6defe9b
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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