Oxalyl chloride → HCID 131732454, compound

HRID 1850892Notes

Reaction equation

HRID 1850892 reaction equation
[Cl:1][C:2]1[C:10]([CH:11]=[N:12][O:13][CH2:14][C:15]#[CH:16])=[C:9]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:21]([N:23]1[C:27]([NH2:28])=[N:26][N:25]=[N:24]1)[CH3:22].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][CH2:14][C:15]#[CH:16])=[C:9]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:8]=[CH:7][C:3]=1[C:4]([NH:28][C:27]1[N:23]([CH2:21][CH3:22])[N:24]=[N:25][N:26]=1)=[O:6]

Participants

9

Reactant 4

HCID 65578Oxalyl chlorideHCID 3078981-ethyl-1H-tetrazol-5-amineHCID 516920Potassium bisulfateHCID 131732455HCID 131732455, compound

Product 1

HCID 131732454HCID 131732454, compound

Reagents, catalysts & solvents 4

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

Conditions

Temperature
70 °C

Procedure

400 mg (1.15 mmol) of 2-chloro-4-(methylsulfonyl)-3-{[(prop-2-yn-1-yloxy)imino]methyl}benzoic acid and 171.60 mg (1.44 mmol) of 1-ethyl-1H-tetrazole-5-amine were dissolved in 4 ml of pyridine, and 10 mg of 4-dimethylaminopyridine and a drop of DMF were added. At RT, 186.65 mg (1.441 mmol) of oxalyl chloride were then added dropwise, and the mixture was stirred at 70° C. for 3 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. Yield: 351.60 mg (67%) as an orange solid.

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

Sources & evidence

ORD record
ord-4a8b1f625d2942d4a70a1c4e73da2f2f
Source dataset
uspto-grants-2015_02
Patent number
US08957096B2

Reaction notes

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