Sodium borohydride → 2,2-Dioxo-3,4-dihydro-6-(1,1-dimethylethyl)-8-iodo-1,2,3-benzoxathiazine

HRID 27400Notes

Reaction equation

HRID 27400 reaction equation
[O:1]=[S:2]1(=[O:17])[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[C:11]([I:12])[C:4]=2[O:3]1.[BH4-].[Na+]>CO>[O:17]=[S:2]1(=[O:1])[NH:7][CH2:6][C:5]2[CH:8]=[C:9]([C:13]([CH3:15])([CH3:14])[CH3:16])[CH:10]=[C:11]([I:12])[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 127618412,2-Dioxo-6-(1,1-dimethylethyl)-8-iodo-1,2,3-benzoxathiazine

Product 1

HCID 127618422,2-Dioxo-3,4-dihydro-6-(1,1-dimethylethyl)-8-iodo-1,2,3-benzoxathiazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2,2-dioxo-6-(1,1-dimethylethyl)-8-iodo-1,2,3-benzoxathiazine (2 g., 5.5 millimole) in methanol (75 ml.) is added sodium borohydride (0.21 g., 5.5 millimole) portionwise with stirring at 20° C. The resulting reaction solution is stirred at 20° C. for 16 hours and then concentrated in vacuo leaving a residual solid which is triturated with water (50 ml.). The insoluble solid is collected and crystallized from 40% ethanol-acetic acid (25:2, v:v) to give 2,2-dioxo-3,4-dihydro-6-(1,1-dimethylethyl)-8-iodo-1,2,3-benzoxathiazine as colorless crystals (1.7 g., 85%), m.p. 154°-155° C.

Workup

  1. customThe resulting reaction solution
  2. stirringis stirred at 20° C. for 16 hours
  3. concentrationconcentrated in vacuo
  4. customleaving a residual solid which
  5. customis triturated with water (50 ml.)
  6. customThe insoluble solid is collected
  7. customcrystallized from 40% ethanol-acetic acid (25:2, v:v)

Sources & evidence

ORD record
ord-3c972579e36b41beb6e0438f82532a9b
Source dataset
uspto-grants-1980_09
Patent number
US04221790

Reaction notes

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