Water → HCID 68089459, compound

HRID 1615672Notes

Reaction equation

HRID 1615672 reaction equation
[N+:1]([C:4]1[C:13]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][C:5]=1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])([O-:3])=[O:2].[H-].[Na+].S(OC)(O[CH3:28])(=O)=O.O>CN(C=O)C>[CH3:28][N:14]([C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:10][CH2:11][O:12][C:13]=2[C:4]=1[N+:1]([O-:3])=[O:2])[C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 68089533HCID 68089533, compound

Product 1

HCID 68089459HCID 68089459, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of tert-butyl 5-nitro-2,3-dihydrobenzo[b][1,4]dioxin-6-ylcarbamate (2.3 g, 7.8 mmol) in DMF (25 mL) was stirred at 0° C. Sodium hydride (373 mg, 9.3 mmol) was added slowly. Dimethyl sulfate (1.017 g, 9.3 mmol) was added dropwise and the mixture was stirred at 0° C. for 0.5 h. To the reaction mixture was slowly added water (40 mL). The mixture was extracted with toluene (40 mL), the organic phase was washed with water (40 mL) and dried, and the solvent removed. The product was purified by silica gel column (5% v/v EtOAc in PE) to give tert-butyl methyl(5-nitro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)carbamate (2.2 g, 92% yield). ESI MS: m/z 311 [M+H]+,

Workup

  1. stirringthe mixture was stirred at 0° C. for 0.5 h
  2. extractionThe mixture was extracted with toluene (40 mL)
  3. washthe organic phase was washed with water (40 mL)
  4. customdried
  5. customthe solvent removed
  6. customThe product was purified by silica gel column (5% v/v EtOAc in PE)

Sources & evidence

ORD record
ord-f6a7b9012f2d4a48b95015d29a7a7180
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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