Aniline → HCID 15022346, compound

HRID 256521Notes

Reaction equation

HRID 256521 reaction equation
[Cl:1][C:2]1[C:3]([C:7](Cl)=[O:8])=[CH:4][S:5][CH:6]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCOCC1.N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([C:7]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[CH:4][S:5][CH:6]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 129147964-Chlorothiophene-3-carbonyl chloride

Product 1

HCID 15022346HCID 15022346, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

At room temperature, a solution of 4-chlorothiophene-3-carboxylic chloride (13.5 g, 0.075 mol) in 30 ml of dioxane is dripped into a solution of aniline (7.7 g, 0.083 mol) in pyridine (160 ml). The mixture is stirred for 12 hours at room temperature and concentrated to dryness, and the residue is taken up in dichloromethane. The organic phase is extracted with aqueous citric acid solution, sodium bicarbonate solution and water, dried and concentrated to dryness. Yield: 16.7 g, 94%; m.p. 119°-121° C.

Workup

  1. customAt room temperature
  2. concentrationconcentrated to dryness
  3. extractionThe organic phase is extracted with aqueous citric acid solution, sodium bicarbonate solution and water
  4. customdried
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4bf6fee78d27453bbfd45471e4bf980e
Source dataset
uspto-grants-1993_11
Patent number
US05258357

Reaction notes

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