Dimethylformamide → HCID 57706798, compound

HRID 1662487Notes

Reaction equation

HRID 1662487 reaction equation
[CH3:1][C:2]([C:5]([C:7]1[CH:12]=[C:11]([C:13](OC)=O)[CH:10]=[CH:9][C:8]=1[C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[F:25])=[CH2:6])([CH3:4])[CH3:3].CN(C=O)C.S(Cl)([Cl:33])=O>C(Cl)Cl>[Cl:33][CH2:13][C:11]1[CH:10]=[CH:9][C:8]([C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=2[F:25])=[C:7]([C:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[CH2:6])[CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 57705563HCID 57705563, compound

Product 1

HCID 57706798HCID 57706798, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 66.18F (0.050 g, 0.16 mmol) in DCM (2.00 mL) at 0 C was added DMF (0.0012 mL), followed by thionyl chloride (0.023 mL, 0.32 mmol). The reaction was then stirred for 1.5 hours and then concentrated in vacuo. The product was purified on silica gel (0-10% EtOAc in hexanes) to yield 69.15A as a colorless oil (0.050 g, 94% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product was purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-27fa2a0b7b9f42f89b8662e222e25210
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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