Oxalyl chloride → HCID 89545072, compound

HRID 1850891Notes

Reaction equation

HRID 1850891 reaction equation
[Cl:1][C:2]1[C:10]([CH:11]=[N:12][O:13][CH3:14])=[C:9]([Cl:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:16]([C:18]1[O:22][C:21]([NH2:23])=[N:20][N:19]=1)[CH3:17].C(Cl)(=O)C(Cl)=O.OS([O-])(=O)=O.[K+]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1.O.CN(C=O)C>[Cl:1][C:2]1[C:10]([CH:11]=[N:12][O:13][CH3:14])=[C:9]([Cl:15])[CH:8]=[CH:7][C:3]=1[C:4]([NH:23][C:21]1[O:22][C:18]([CH2:16][CH3:17])=[N:19][N:20]=1)=[O:6]

Participants

9

Reactant 4

HCID 65578Oxalyl chlorideHCID 3434875-Ethyl-1,3,4-oxadiazol-2-amineHCID 516920Potassium bisulfateHCID 86200989HCID 86200989, compound

Product 1

HCID 89545072HCID 89545072, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

400 mg (1.61 mmol) of 2,4-dichloro-3-[(methoxyimino)methyl]benzoic acid and 228 mg (2.0 mmol) of 5-ethyl-1,3,4-oxadiazole-2-amine were dissolved in 3 ml of pyridine, and 10 mg of 4-dimethylaminopyridine and a drop of DMF were added. At room temperature (RT), 255.83 mg (2.016 mmol) of oxalyl chloride were then added dropwise, and the mixture was stirred at 70° C. for 4 h. 0.5 ml of water was then added to the reaction, which had once more been cooled, and the mixture was stirred for about 30 min, acidified with a saturated KHSO4 solution and extracted three times with in each case 100 ml of ethyl acetate. The combined organic phases were washed once with 20 ml of a saturated NaHCO3 solution, dried over MgSO4, filtered off and concentrated. The residue was purified chromatographically by preparative HPLC. Yield: 99.3 mg (18%) as colorless crystals.

Workup

  1. temperaturehad once more been cooled
  2. stirringthe mixture was stirred for about 30 min
  3. extractionextracted three times with in each case 100 ml of ethyl acetate
  4. washThe combined organic phases were washed once with 20 ml of a saturated NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered off
  7. concentrationconcentrated
  8. customThe residue was purified chromatographically by preparative HPLC

Sources & evidence

ORD record
ord-112c55b5d7c74960a1e0cd20742b360c
Source dataset
uspto-grants-2015_02
Patent number
US08957096B2

Reaction notes

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