Thionyl Chloride → HCID 89545295, compound

HRID 1850893Notes

Reaction equation

HRID 1850893 reaction equation
[Cl:1][C:2]1[C:10]([CH2:11][O:12][N:13]=[C:14]([CH3:16])[CH3:15])=[C:9]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:21][N:22]1[C:26]([NH2:27])=[N:25][CH:24]=[N:23]1.S(Cl)(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]([CH2:11][O:12][N:13]=[C:14]([CH3:16])[CH3:15])=[C:9]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:8]=[CH:7][C:3]=1[C:4]([NH:27][C:26]1[N:22]([CH3:21])[N:23]=[CH:24][N:25]=1)=[O:5]

Participants

9

Reactant 4

HCID 24386Thionyl ChlorideHCID 516920Potassium bisulfateHCID 5665971-methyl-1h-1,2,4-triazol-5-amineHCID 117643149HCID 117643149, compound

Product 1

HCID 89545295HCID 89545295, compound

Reagents, catalysts & solvents 4

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

Conditions

Temperature
70 °C

Procedure

500 mg (1.56 mmol) of 2-chloro-4-(methylsulfonyl)-3-{[(propan-2-ylideneamino)oxy]methyl}benzoic acid and 395 mg (1.34 mmol) of 1-methyl-1H-1,2,4-triazole-5-amine were dissolved in 2.5 ml of pyridine, and 10 mg of 4-dimethylaminopyridine and a drop of DMF were added. At RT, 313 mg (2.58 mmol) of thionyl chloride were then added dropwise, and the mixture was stirred at 70° C. for 5 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 on a silica gel column. Yield: 153 mg (24%) as a colorless oil.

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 on a silica gel column

Sources & evidence

ORD record
ord-ca0e6b510f6745189b9b45de640ec056
Source dataset
uspto-grants-2015_02
Patent number
US08957096B2

Reaction notes

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