Methyl iodide → 1,1-Dimethylethyl cyclopropyl({2,3-dichloro-5-[2-(methyloxy)ethyl]phenyl}methyl)carbamate

HRID 337553Notes

Reaction equation

HRID 337553 reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][CH2:20][OH:21])[CH:16]=[C:15]([Cl:22])[C:14]=2[Cl:23])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.[H-].[Na+].I[CH3:27]>C1COCC1>[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][CH2:20][O:21][CH3:27])[CH:16]=[C:15]([Cl:22])[C:14]=2[Cl:23])[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 668971121,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(2-hydroxyethyl)phenyl]methyl}carbamate

Product 1

HCID 668992901,1-Dimethylethyl cyclopropyl({2,3-dichloro-5-[2-(methyloxy)ethyl]phenyl}methyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(2-hydroxyethyl)phenyl]-methyl}carbamate (1 eq.) was taken up in THF (0.3 M). To this solution was then added sodium hydride (60% w/w dispersion in oil, 1 eq.) and the resulting suspension was stirred at RT for 5 min. Finally, iodomethane (10 eq.) was added and the now pale yellow solution was stirred in darkness at RT for another 10 h. The volatiles were then removed in vacuo and the resulting residue partitioned between ether and 1 N aq. HCl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed further with 1 N aq. NaOH, water and brine. This was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to give the title compound (contaminated with oil) as a pale yellow oil.

Workup

  1. customThe volatiles were then removed in vacuo
  2. customthe resulting residue partitioned between ether and 1 N aq. HCl
  3. customThe aqueous layer was separated
  4. extractionback-extracted with ether
  5. washThe combined organic extracts were then washed further with 1 N aq. NaOH, water and brine
  6. dry with materialThis was then dried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-49e99c13d8a04f3c847874fb4e95446f
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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