Hydrochloric Acid → HCID 117600520, compound

HRID 1505596Notes

Reaction equation

HRID 1505596 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[F:27][C:28]([F:39])([F:38])[CH2:29][O:30][C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34].Cl>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([NH:34][C:33]1[CH:35]=[CH:36][CH:37]=[C:31]([O:30][CH2:29][C:28]([F:27])([F:38])[F:39])[CH:32]=1)=[O:6]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 792872-Chloro-6-nitrobenzoic acidHCID 47709443-(2,2,2-trifluoroethoxy)aniline

Product 1

HCID 117600520HCID 117600520, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Under nitrogen, to 2-chloro-6-nitrobenzoic acid (1.27 g, 6.28 mmol, 1.00 equiv) in CH2Cl2 (20 mL) at 23° C. was added oxalyl chloride (0.585 mL, 6.91 mmol, 1.10 equiv) and DMF (16 μL, 0.19 mmol, 3.0 mol %). After stirring for 1 hr at 23° C., the reaction mixture was cooled to 0° C. and triethylamine (2.63 mL, 18.8 mmol, 3.00 equiv) and 3-(2,2,2-trifluoroethoxy)aniline (1.20 g, 6.28 mmol, 1.00 equiv) were added. After stirring for 15 min at 0° C., 3N HCl aq (50 mL) was added. The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×3.0 mL). The combined organic phases were washed with brine (3.0 mL) and dried (MgSO4). The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc to afford 965 mg of the title compound (41% yield).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. stirringAfter stirring for 15 min at 0° C.
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (3×3.0 mL)
  5. washThe combined organic phases were washed with brine (3.0 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc

Sources & evidence

ORD record
ord-1eaca08c7d6743d7a71687ae851ebb56
Source dataset
uspto-grants-2015_12
Patent number
US09216985B2

Reaction notes

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