Triethylamine → HCID 54474120, compound

HRID 903017Notes

Reaction equation

HRID 903017 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[CH:12][CH:11]=1)([O-:9])=[O:8].C([N:26]([CH2:29][CH3:30])CC)C>O1CCCC1>[N+:7]([C:10]1[CH:15]=[CH:30][C:29]([N:26]([S:17]([C:20]([F:23])([F:21])[F:22])(=[O:18])=[O:19])[C:2]([C:1]([N:16]([C:13]2[CH:12]=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:15][CH:14]=2)[S:17]([C:20]([F:23])([F:21])[F:22])(=[O:19])=[O:18])=[O:5])=[O:3])=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 394807HCID 394807, compound

Product 1

HCID 54474120HCID 54474120, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (0.825 gram; 0.0065 mole) is added dropwise to a stirred solution of N-4-nitrophenyl trifluoromethanesulfonamide (3.61 grams; 0.013 mole) and triethylamine (1.3 grams; 0.0128 mole) in dry tetrahydrofuran (40 mls) at 0° C. under a nitrogen atmosphere. After the addition is completed, the reaction mixture is warmed to room temperature and stirred thereat for 18 hours. The reaction mixture is then filtered, the solvent is evaporated from the filtrate, and water (20 mls) is added to the residue. The resulting precipitate is then filtered to obtain 3.29 grams (92% of theoretical) of crude yellow-colored product.

Workup

  1. additionAfter the addition
  2. filtrationThe reaction mixture is then filtered
  3. customthe solvent is evaporated from the filtrate, and water (20 mls)
  4. additionis added to the residue
  5. filtrationThe resulting precipitate is then filtered
  6. customto obtain 3.29 grams (92% of theoretical) of crude yellow-colored product

Sources & evidence

ORD record
ord-caaad02c4e2b43f3a9e3e5a4a4a03631
Source dataset
uspto-grants-1980_10
Patent number
US04226738

Reaction notes

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