Benzene → HCID 12362919, compound

HRID 435622Notes

Reaction equation

HRID 435622 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]2[S:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[CH:11](O)[CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].C1C=CC=CC=1.C(Cl)(Cl)[Cl:27].S(Cl)(Cl)=O>N1C=CC=CC=1.O>[Cl:27][CH:11]1[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[S:8][C:7]2[CH:18]=[CH:19][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[CH2:12]1

Participants

7

Reactant 4

HCID 241BenzeneHCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 12362918HCID 12362918, compound

Product 1

HCID 12362919HCID 12362919, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

124 g of 10,11-dihydro-2-nitro-dibenzo[b,f]thiepin- 10-ol are suspended in 69.5 ml of pyridine, 615 ml of benzene and 350 ml of chloroform and the mixture is treated dropwise with stirring at 0° C with 53 ml of thionyl chloride. The mixture is stirred overnight at room temperature and then for a further 30 minutes at 35° - 40° C, cooled and diluted with water. The organic phase is washed successively with water and aqueous sodium bicarbonate solution, dried over magnesium sulphate and evaporated. There is obtained 10-chloro-10,11 -dihydro-2-nitro-dibenzo[b,f]thiepin of melting point 74° - 77° C.

Workup

  1. waitfor a further 30 minutes at 35° - 40° C
  2. temperaturecooled
  3. washThe organic phase is washed successively with water and aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-913ee77e659d4f468a25fa390f5c74dd
Source dataset
uspto-grants-1977_02
Patent number
US04006145

Reaction notes

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