Sodium Bicarbonate → 1,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(2-oxoethyl)phenyl]methyl}carbamate

HRID 337559Notes

Reaction equation

HRID 337559 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.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][CH:20]=[O:21])[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

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 668971121,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(2-hydroxyethyl)phenyl]methyl}carbamate

Product 1

HCID 866516621,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(2-oxoethyl)phenyl]methyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(2-hydroxyethyl)phenyl]methyl}carbamate (1 eq.) from Step 3, Amine 6 and sodium bicarbonate (1 eq.) were suspended in CH2Cl2 (0.1 M). At 0° C., DMP (1 eq.) was added and the resulting mixture was stirred at 0° C. for 15 min and then at RT for 45 min. The reaction was quenched with 1 N aq. NaOH and extracted with ether. The combined organic extracts were then washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the title compound as an unstable, colorless oil.

Workup

  1. additionAt 0° C., DMP (1 eq.) was added
  2. waitat RT for 45 min
  3. customThe reaction was quenched with 1 N aq. NaOH
  4. extractionextracted with ether
  5. washThe combined organic extracts were then washed further with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-916a2246be1d445c971690d33240c4bb
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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