Triethylamine → HCID 21161676, compound

HRID 2286314Notes

Reaction equation

HRID 2286314 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.O1CCOCC1.Cl[CH2:27][CH2:28][S:29]([F:32])(=[O:31])=[O:30]>O>[F:32][S:29]([CH2:28][CH2:27][NH:4][C:3]1[CH:5]=[C:6]([NH:9][C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][C:2]=1[CH3:1])(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 22865N-(3-amino-4-methylphenyl)acetamideHCID 312751,4-DioxaneHCID 69807Ethanesulfonyl fluoride, 2-chloro-

Product 1

HCID 21161676HCID 21161676, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Methyl-5-acetamido aniline (49.2 g, 0.3 m), triethyl amine (32.7 g, 0.3 m) and p-dioxane (350 ml) are stirred together at room temperature. 2-Chloroethane sulfonylfluoride (43.0 g, 0.3 m) is added dropwise allowing temperature to rise to 45° C. The reaction mixture is then heated at reflux for 3 hrs. When thin-layer chromatography shows reaction to be complete, the reaction is allowed to cool and then drowned into water (2000 ml). The product is collected by filtration, washed with water and melts at 154°-155° C.

Workup

  1. customto rise to 45° C
  2. temperatureThe reaction mixture is then heated
  3. temperatureat reflux for 3 hrs
  4. customreaction
  5. temperatureto cool
  6. filtrationThe product is collected by filtration
  7. washwashed with water and melts at 154°-155° C.

Sources & evidence

ORD record
ord-8e1f869763f14df1b1f72fcc59931f3b
Source dataset
uspto-grants-1981_05
Patent number
US04265812

Reaction notes

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