Sulfuric Acid → HCID 12362918, compound

HRID 435681Notes

Reaction equation

HRID 435681 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[C:11](=[O:13])[CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].S(=O)(=O)(O)O>O1CCOCC1.O>[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]([OH:13])[CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 12362917HCID 12362917, compound

Product 1

HCID 12362918HCID 12362918, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

165.3 g of 10,11-dihydro-2-nitro-dibenzo[b,f]thiepin-10-one are suspended in 6 litres of dioxane and treated with a solution of 63 g of sodium borohydride in 300 ml of dioxane and 300 ml of water. The mixture is stirred overnight at room temperature, then diluted with water, made neutral with sulphuric acid and extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulphate and evaporated under reduced pressure. The 10,11-dihydro-2-nitro-dibenzo[b,f]thiepin-10-ol obtained is recrystallised from ethyl acetate; melting point 144°-146° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c75d08418e4a48328b177e1fbf8f3e00
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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