Sulfolane → 7-Nitro-3,4-dihydro-2H-1,5-benzodioxepin-3-spiro-2'-oxirane

HRID 267773Notes

Reaction equation

HRID 267773 reaction equation
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].C1S(=O)(=O)CCC1.[O:16]1[CH2:18][C:17]21[CH2:24][O:23][C:22]1[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=1[O:20][CH2:19]2>>[N+:7]([C:27]1[CH:26]=[CH:25][C:22]2[O:23][CH2:24][C:17]3([CH2:19][O:20][C:21]=2[CH:28]=1)[CH2:18][O:16]3)([O-:8])=[O:6]

Participants

4

Reactant 3

HCID 31347SulfolaneHCID 11073463Nitronium tetrafluoroborateHCID 155573103,4-dihydro-2H-1,5-benzodioxepin-3-spiro-2'-oxirane

Product 1

HCID 888457837-Nitro-3,4-dihydro-2H-1,5-benzodioxepin-3-spiro-2'-oxirane

Conditions

Temperature
35 °C

Procedure

A mixture of 0.11 mole of nitronium tetrafluoroborate and 60 g. tetramethylene sulfone is stirred at 10° C. and 0.1 mole of 3,4-dihydro-2H-1,5-benzodioxepin-3-spiro-2'-oxirane, prepared as described in Example 57, Step A, added during 30 minutes. The cooling bath then is removed and the mixture stirred an additional 20 minutes at 35° C., poured into ice and water, the product extracted with ether, the ether solution dried over magnesium sulfate and evaporated. The product obtained following crystallization from a mixture of chloroform and petroleum ether is 7-nitro-3,4-dihydro-2H-1,5-benzodioxepin-3-spiro-2'-oxirane.

Workup

  1. additionadded during 30 minutes
  2. customThe cooling bath then is removed
  3. additionpoured into ice and water
  4. extractionthe product extracted with ether
  5. dry with materialthe ether solution dried over magnesium sulfate
  6. customevaporated
  7. customThe product obtained
  8. customcrystallization
  9. additionfrom a mixture of chloroform and petroleum ether

Sources & evidence

ORD record
ord-e92dbae298bf46838bac36d9cfea7e1d
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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