Dichloromethane → HCID 57884082, compound

HRID 1818053Notes

Reaction equation

HRID 1818053 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:14])[CH2:5][C:6]([CH3:13])([CH3:12])[O:7]2.[I:15](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](CC)(CC)CC)C1C=CC=CC=1.C(=O)(O)[O-].[Na+].C(Cl)Cl>CO>[NH2:1][C:2]1[C:11]([I:15])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:14])[CH2:5][C:6]([CH3:12])([CH3:13])[O:7]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 53418337HCID 53418337, compound2×HCID 86614807HCID 86614807, compound

Product 1

HCID 57884082HCID 57884082, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a 100 mL round bottom flask equipped with a magnetic stir bar was added 6 (234 mg, 1.23 mmol), benzyltriethylammonium dichloroiodate (11, 480 mg, 1.23 mmol), sodium bicarbonate (113 mg, 1.35 mmol), CH2Cl2 (5 mL) and reagent grade methanol (2 mL). The flask was equipped with a water condenser, and the mixture was heated to 40° C. with stirring until all of compound 6 was consumed, as determined by TLC analysis. CH2Cl2 (10 mL) and 10% aqueous sodium bisulfite (10 ml) were added, the organic phase was washed with brine (1×10 mL), dried over MgSO4, filtered, concentrated and dried under high vacuum. The dry, crude product was passed through a silica gel column using straight CH2Cl2 (Rf=0.5) as eluent. The reaction provided 171 mg (44%) of 7 as a yellow solid. 1H NMR (300 MHZ, CDCl3): δ 7.58 (d, J=9 Hz, 1H), 6.00 (d, J=9 Hz, 1H), 2.67 (s, 2H), 1.40 (s, 6H). 13C NMR (75.5 MHZ, CDCl3): δ 193.9, 161.3, 149.6, 145.4, 106.9, 105.8, 78.2, 73.6, 48.8, 26.5. HRMS (EI+): calculated for C11H12INO2 [M+] m/z 316.9913, found 316.9906.

Workup

  1. customTo a 100 mL round bottom flask equipped with a magnetic stir bar
  2. customThe flask was equipped with a water condenser
  3. customwas consumed
  4. additionCH2Cl2 (10 mL) and 10% aqueous sodium bisulfite (10 ml) were added
  5. washthe organic phase was washed with brine (1×10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-1611cf6d8baf415eb767c61ce0e1610e
Source dataset
uspto-grants-2009_10
Patent number
US07598403B2

Reaction notes

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