Sodium Chloride → HCID 89827399, compound

HRID 2207314Notes

Reaction equation

HRID 2207314 reaction equation
[C:1]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]([CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=2[CH2:25]O)[C:6]1=[O:27])([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:30])=O.[Na+].[Cl-]>ClCCl.CN(C=O)C>[C:1]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]([CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=2[CH2:25][Cl:30])[C:6]1=[O:27])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 24386Thionyl ChlorideHCID 89827393HCID 89827393, compound

Product 1

HCID 89827399HCID 89827399, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 15 (3.5 g, 10.4 mmol) in dichloromethane (20 mL) was charged DMF (0.04 mL, 0.5 mmol). This solution was cooled under an ice bath. Thionyl chloride (0.85 mL, 11.5 mmol) was then added under 5° C., and the resulting reaction was aged for 3 h at this temperature. Once the reaction was complete, 5% aqueous NaCl (16.5 mL) was added. The organic layer was separated and washed with 5% aqueous NaCl (16.5 mL). The solvent was removed via rotovap, and the crude was purified by silica gel column chromatography (0 to 10% AcOEt/hexane) to give the desired compound 16 as an oil (3.05 g, 74%). 1H NMR (CDCl3, 500 MHz): δ 8.20 (dd, J=5.1, 1.7 Hz, 1H), 7.58 (d, J=8.1 Hz, 1H), 7.51 (dd, J=8.1, 1.1 Hz, 1H), 7.18 (s, 1H), 7.12 (dd, J=6.3, 2.7 Hz, 1H), 6.88 (dd, J=7.3, 5.1 Hz, 1H), 4.77 (ABq, J=12.9 Hz, 2H), 3.72 (m, 1H), 3.46 (dd, J=14.2, 4.4, 1H), 3.18 (dd, J=14.2, 8.7 Hz, 1H), 1.67 (s, 9H); 13C NMR (CDCl3, 125 MHz): δ 177.6, 159.1, 146.5, 143.3, 136.6, 131.0, 129.7 (m, 2C), 124.0, 123.0, 123.9 (q, J=271 Hz), 117.4, 126.6, 62.4, 58.8, 46.1, 32.9, 28.6.

Workup

  1. temperatureThis solution was cooled under an ice bath
  2. customthe resulting reaction
  3. customThe organic layer was separated
  4. washwashed with 5% aqueous NaCl (16.5 mL)
  5. customThe solvent was removed via rotovap
  6. customthe crude was purified by silica gel column chromatography (0 to 10% AcOEt/hexane)

Sources & evidence

ORD record
ord-652df48ca59d45378e29d836bc273530
Source dataset
uspto-grants-2016_06
Patent number
US09376431B2

Reaction notes

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