Dimethylformamide → HCID 20781264, compound

HRID 2181269Notes

Reaction equation

HRID 2181269 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])[CH2:16][CH2:15][CH:14]([NH:17][S:18]([CH2:21][C:22]([NH2:24])=O)(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.CN(C)C=O>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])[CH2:12][CH2:13][CH:14]([NH:17][S:18]([CH2:21][C:22]#[N:24])(=[O:20])=[O:19])[CH2:15][CH2:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22485770HCID 22485770, compound

Product 1

HCID 20781264HCID 20781264, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of the amide of Example 44 (80 mg, 0.16 mmol) in toluene (10 ml) under nitrogen was added thionyl chloride (23 μL, 0.32 mmol) and a catalytic amount of dimethylformamide. After refluxing for 16 h, the reaction was cooled to ambient temperature, diluted with water and extracted with ethyl acetate The combined organic layers were washed with brine, dried (MgSO4) and evaporated to give a residue (78 mg) which was purified using preparative thin layer chromatography eluting with ethyl acetate:hexane 1:2 to give the desired product (42 mg). 1H NMR (CDCl3) 7.39-7.31 (4H, m), 7.08-7.04 (2H, m), 6.88-6.84 (1H, m), 6.24 (1H, d, J=6.1 Hz), 4.12 (2H, s), 3.09-3.07 (1H, m), 2.62-2.46 (4H, m), 2.11-2.04 (2H, m), 1.65-1.57 (2H, m). M/z(ES−)=487/489

Workup

  1. temperatureAfter refluxing for 16 h
  2. extractionextracted with ethyl acetate The combined organic layers
  3. washwere washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-4d8f579f47cf476eb44fbee0580ca2d5
Source dataset
uspto-grants-2005_05
Patent number
US06890956B2

Reaction notes

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