Formic Acid → HCID 71254646, compound

HRID 539971Notes

Reaction equation

HRID 539971 reaction equation
[N:1]([CH2:4][C:5]1([CH2:9][N:10]=[N+:11]=[N-:12])[CH2:8][S:7][CH2:6]1)=[N+:2]=[N-:3].C(O)=[O:14].ClCCl.OO.[OH2:21]>>[N:10]([CH2:9][C:5]1([CH2:4][N:1]=[N+:2]=[N-:3])[CH2:6][S:7](=[O:14])(=[O:21])[CH2:8]1)=[N+:11]=[N-:12]

Participants

6

Reactant 5

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 6344DichloromethaneHCID 86691371HCID 86691371, compound

Product 1

HCID 71254646HCID 71254646, compoundYield 96%

Procedure

To a solution of 3,3-bis(azidomethyl)thietane (2.5 g, 13.59 mmol) in the mixture of formic acid (5 mL) and dichloromethane (6 mL) was added hydrogen peroxide (9.2 g, 81.54 mmol) slowly at 0° C. After being warmed slowly to room temperature and stirred at room temperature overnight, the mixture was diluted with water (10 mL) and extracted with dichloromethane (15 mL×3). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography to afford 2.8 g of the desired product as a white solid (yield of two steps was 96%).

Workup

  1. extractionextracted with dichloromethane (15 mL×3)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-39de7b409c7040e9a63a37b37b287bd5
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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