Diphenylamine → HCID 12479605, compound

HRID 345462Notes

Reaction equation

HRID 345462 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:14][CH2:15][CH2:16][CH2:17][C:18](Cl)=[O:19]>O1CCCC1>[Cl:14][CH2:15][CH2:16][CH2:17][C:18]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:19]

Participants

4

Reactant 2

HCID 11487DiphenylamineHCID 783704-Chlorobutyryl chloride

Product 1

HCID 12479605HCID 12479605, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution 22.8 g (0.14 mole) of diphenylamine in 150 ml of tetrahydrofuran was added dropwise to a solution of 9.9 g (0.07 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 give a yellow solid. The solid was purified by column chromatography using 300 g of silica gel on a 65 cm×4 cm column, eluted with 10% ethyl acetate in hexane. The fractions containing the desired product were combined and concentrated under reduced pressure to yield 16.8 g (88%) of white, crystalline solid, mp 78°-79° 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
  7. customto give a yellow solid
  8. customThe solid was purified by column chromatography
  9. washeluted with 10% ethyl acetate in hexane
  10. additionThe fractions containing the desired product
  11. concentrationconcentrated under reduced pressure
  12. customto yield 16.8 g (88%) of white, crystalline solid, mp 78°-79° C.

Sources & evidence

ORD record
ord-617374bfbc7f4d759b93f5b11cef51ab
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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