Hydrochloric Acid → HCID 89689493, compound

HRID 514174Notes

Reaction equation

HRID 514174 reaction equation
[Cl-].[Mg+2].[Cl-].C(CC(OCC1C=CC=CC=1)=O)#N.C(N(CC)CC)C.CS(C1C=C(C(F)(F)F)C=CC=1C(Cl)=O)(=O)=O.Cl.[CH3:42][S:43]([C:46]1[CH:66]=[C:65]([C:67]([F:70])([F:69])[F:68])[CH:64]=[CH:63][C:47]=1[C:48]([CH:50]([C:61]#[N:62])C(OCC1C=CC=CC=1)=O)=[O:49])(=[O:45])=[O:44]>C(#N)C.C1COCC1>[CH3:42][S:43]([C:46]1[CH:66]=[C:65]([C:67]([F:68])([F:70])[F:69])[CH:64]=[CH:63][C:47]=1[C:48]([CH2:50][C:61]#[N:62])=[O:49])(=[O:45])=[O:44]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 560818Benzyl 2-cyanoacetateHCID 5360315Magnesium ChlorideHCID 11808291Benzoyl chloride, 2-(methylsulfonyl)-4-(trifluoromethyl)-HCID 117700212HCID 117700212, compound

Product 1

HCID 89689493HCID 89689493, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.10 g of magnesium chloride (11.5 mmol) in 15 ml of acetonitrile are admixed at 0° C. with 2.0 g (11.4 mmol) of benzyl cyanoacetate and 2.3 g (22.9 mmol) of triethylamine. After stirring for 20 min at 0° C., 3.27 g (11.4 mmol) of 2-(methylsulfonyl)-4-trifluoromethylbenzoyl chloride are added in portions. The mixture is stirred for 16 h at RT, acidified with 2n HCl and extracted with ether. The organic phase is dried and concentrated in a rotary evaporator. Yield 2.74 g (56%; 1H-NMR, CDCl3, 400 MHz: 14.20 (bs, 1H), 8.43 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 5.40 (s, 2H), 3.30 (s, 3H)) of benzyl 2-(2-(methylsulfonyl)-4-trifluoromethylbenzoyl)cyanoacetate, which, after adding 0.65 g (1 eq) of triethylamine in THF, is hydrogenated for 2 h. After filtration, the mixture is diluted with ethyl acetate and washed with 2N HCl, NaHCO3 solution and sodium chloride solution. Yield 1.41 g (75%). 1H NMR, CDCl3, 400 MHz: 8.36 (s, 1H), 8.04 (d, 1H), 7.63 (d, 1H), 4.03 (s, 2H), 3.21 (s, 3H).

Workup

  1. stirringThe mixture is stirred for 16 h at RT
  2. extractionextracted with ether
  3. customThe organic phase is dried
  4. concentrationconcentrated in a rotary evaporator
  5. waitis hydrogenated for 2 h
  6. filtrationAfter filtration
  7. additionthe mixture is diluted with ethyl acetate
  8. washwashed with 2N HCl, NaHCO3 solution and sodium chloride solution

Sources & evidence

ORD record
ord-95453910868648c3b1df1af2ca1bf56c
Source dataset
uspto-grants-2015_08
Patent number
US09107414B2

Reaction notes

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