Ammonia → HCID 11392109, compound

HRID 2240878Notes

Reaction equation

HRID 2240878 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:14][CH2:15][F:16])[CH2:10][C:11](O)=[O:12])=[CH:5][C:4]=1[C:17]([F:20])([F:19])[F:18])#[N:2].C(Cl)(=O)C(Cl)=O.C[N:28](C=O)C.N>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:14][CH2:15][F:16])[CH2:10][C:11]([NH2:28])=[O:12])=[CH:5][C:4]=1[C:17]([F:20])([F:19])[F:18])#[N:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 57633776HCID 57633776, compound

Product 1

HCID 11392109HCID 11392109, compoundYield 303.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(2-fluoroethyl)glycine (0.031 g, 0.11 mmol) in anhydrous CH2Cl2 (2 mL), under nitrogen, was cooled in an ice bath and treated with oxalyl chloride (0.017 g, 0.13 mmol) and anhydrous DMF (˜0.001 g). The mixture was heated at 50° C. for 20 min. Upon cooling, the mixture was added into an aqueous solution of ammonia (30%, 10 mL) and stirred heavily for 5 min. The mixture was partitioned between CH2Cl2 (20 mL), water (20 mL) and methanol (5 mL). The aqueous phase was extracted 3 times with CH2Cl2/MeOH (˜10:1). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from CH2Cl2/MeOH to give 0.012 g (40% yield) of the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 7.79 (d, J=8.8 Hz, 1H), 7.52 (bs, 1H), 7.21 (bs, 1H), 6.99 (d, J=2.4 Hz, 1H), 6.93 (dd, J=8.8, 2.4 Hz, 1H), 4.61 (dt, J=47.4, 4.9 Hz, 2H), 4.08 (s, 2H), 3.82 (dt, J=26.0, 4.9 Hz, 2H).

Workup

  1. temperatureunder nitrogen, was cooled in an ice bath
  2. temperatureUpon cooling
  3. customThe mixture was partitioned between CH2Cl2 (20 mL), water (20 mL) and methanol (5 mL)
  4. extractionThe aqueous phase was extracted 3 times with CH2Cl2/MeOH (˜10:1)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from CH2Cl2/MeOH

Sources & evidence

ORD record
ord-b2f451a0d7804cfe86aeb6d82c226e09
Source dataset
uspto-grants-2010_05
Patent number
US07723385B2

Reaction notes

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