Aniline → HCID 15022346, compound

HRID 1197420Notes

Reaction equation

HRID 1197420 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

4-Chlorothiophene-3-carbonyl chloride (13.5 g, 0.075 mol) are dissolved in 30 ml of dioxane and the solution is added dropwise at room temperature to a solution of aniline (7.7 g, 0.083 mol) in pyridine (160 ml). Stirring is carried out for 12 hours at room temperature, after which the mixture is evaporated 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 evaporated to dryness. Yield: 16.7 g, 94%; mp. 119° to 121° C.

Workup

  1. customafter which the mixture is evaporated to dryness
  2. extractionThe organic phase is extracted with aqueous citric acid solution, sodium bicarbonate solution and water
  3. customdried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-e533f948fa68494bbe427882048557a2
Source dataset
uspto-grants-1994_01
Patent number
US05276009

Reaction notes

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