Aniline → HCID 5106095, compound

HRID 345461Notes

Reaction equation

HRID 345461 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][CH2:9][CH2:10][CH2:11][C:12](Cl)=[O:13]>O1CCCC1>[Cl:8][CH2:9][CH2:10][CH2:11][C:12]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:13]

Participants

4

Reactant 2

HCID 6115AnilineHCID 783704-Chlorobutyryl chloride

Product 1

HCID 5106095HCID 5106095, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 27.9 g (0.30 mole) of aniline in 100 ml of tetrahydrofuran was added dropwise to a solution of 21.2 g (0.15 mole) of 4-chlorobutyryl chloride in 100 ml of tetrahydrofuran. The reaction mixture was stirred mechanically and the temperature maintained between 5° C. and 15° C. throughout the addition. After the final addition, the solution was filtered to remove solid precipitates and the filtrate was concentrated under reduced pressure to yield 28.9 g (100%) of yellow solid. An analytical sample was prepared by recrystallizing the solid from benzene/petroleum ether (30°-60° C.) to give a white solid, mp 64°-66° C.

Workup

  1. temperaturethe temperature maintained between 5° C. and 15° C. throughout the addition
  2. additionAfter the final addition
  3. filtrationthe solution was filtered
  4. customto remove solid
  5. customprecipitates
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3e7868cd90c9456f830e4e5d66207b2e
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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