Dichloromethane → HCID 11604158, compound

HRID 493443Notes

Reaction equation

HRID 493443 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]([C:16]3([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[CH2:21][CH2:20][N:19](C)[CH2:18][CH2:17]3)[C:12]2=[O:30])[CH:6]=[C:7]([Cl:9])[CH:8]=1.CC(Cl)OC(Cl)=O.C(Cl)Cl.C([O-])(O)=O.[Na+]>ClCCCl>[NH4+:11].[OH-:30].[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]([C:16]3([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:12]2=[O:30])[CH:6]=[C:7]([Cl:9])[CH:8]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 5213051-Chloroethyl chloroformate2×HCID 67527719HCID 67527719, compound

Product 2

HCID 14923Ammonium HydroxideYield 0.5%HCID 11604158HCID 11604158, compoundYield 118.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of example 2 (11 mg), 1-chloroethyl chloridocarbonate (4 μL) and TEA (6.5 μL) in anhydrous 1,2-dichloroethane (100 μL) was refluxed under a Nitrogen atmosphere for 1 h. Additional 1-chloroethyl chloridocarbonate (3×4 μL) and TEA (3×6.5 μL) were added during the following 5 h while stirring. The mixture was concentrated under vacuum, MeOH (200 μL) was added to the residue and resulting mixture refluxed for 1 h. DCM and an aqueous std NaHCO3 solution were added to the crude residue and the aqueous phase extracted with DCM. The organic extracts were collected, dried and evaporated under vacuum to give a crude which was purified by flash cromathography (eluting with DCM:MeOH=95:5 to 9:1, then 8:2 containing 0.5% NH4OH) to afford the title compound (5.8 mg) as a off-white foam.

Workup

  1. concentrationThe mixture was concentrated under vacuum, MeOH (200 μL)
  2. additionwas added to the residue
  3. customresulting mixture
  4. temperaturerefluxed for 1 h
  5. extractionthe aqueous phase extracted with DCM
  6. customThe organic extracts were collected
  7. customdried
  8. customevaporated under vacuum
  9. customto give a crude which
  10. customwas purified by flash cromathography (
  11. washeluting with DCM

Sources & evidence

ORD record
ord-63cc0cb6e8b546dea019256caaa3ddcc
Source dataset
uspto-grants-2009_05
Patent number
US07534893B2

Reaction notes

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