Carbon Tetrachloride → HCID 57633751, compound

HRID 2240882Notes

Reaction equation

HRID 2240882 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:10][C:11]([NH2:13])=O)=[CH:5][C:4]=1[C:19]([F:22])([F:21])[F:20])#[N:2].C(Cl)(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCCl>[C:11]([CH2:10][N:9]([CH2:14][C:15]([F:16])([F:18])[F:17])[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([C:19]([F:21])([F:22])[F:20])[CH:5]=1)#[N:13]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 11472813GSK232420A

Product 1

HCID 57633751HCID 57633751, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
87 °C

Procedure

A mixture of N2-[4-cyano-3-(trifluoromethyl)phenyl]-N2-(2,2,2-trifluoroethyl)glycinamide (0.060 g, 0.18 mmol), CCl4 (0.5 mL), DCE (4.5 mL) and polymer-supported triphenyl phosphine (3 mmol/g, 0.123 g, 0.36 mmol) was heated at 87° C. for 3 h. Upon cooling, the resin was filtered off, washed thoroughly with CHCl3 and the filtrate concentrated in vacuo. The residue was purified by silica gel chromatography (5-40% EtOAc-hexane gradient) and the product was crystallized from CH2Cl2-hexanes to give the title compound as a white solid (0.030 g, 55% yield): 1HNMR (400 MHz, CDCl3) δ 7.90 (d, J=8.6 Hz, 1H), 7.20 (d, J=2.6 Hz, 1H), 7.09 (dd, J=8.6, 2.6 Hz, 1H), 4.38 (s, 2H), 4.06 (q, J=8.2 Hz, 2H); MS (ES) m/z 308 (M+1).

Workup

  1. temperatureUpon cooling
  2. filtrationthe resin was filtered off
  3. washwashed thoroughly with CHCl3
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (5-40% EtOAc-hexane gradient)
  6. customthe product was crystallized from CH2Cl2-hexanes

Sources & evidence

ORD record
ord-cb08a6d6980040b0b48d23e965375d65
Source dataset
uspto-grants-2010_05
Patent number
US07723385B2

Reaction notes

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