Diphenylamine → HCID 19876175, compound

HRID 1886487Notes

Reaction equation

HRID 1886487 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[CH2:15][C:16]#[C:17][CH2:18]Cl>C(OCC)C>[C:8]1([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:15][C:16]#[C:17][CH2:18][N:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 11487DiphenylamineHCID 131821,4-Dichloro-2-butyne

Product 1

HCID 19876175HCID 19876175, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
85 °C

Procedure

A vigorously stirred mixture of diphenylamine (174 g, 1.03 mol) and 1,4-dichlorobut-2-yne (23 g, 0.19 mol) is heated at 85° C. for 72 hours. The black mixture is allowed to cool to room temperature and is then taken up in diethyl ether. Diphenylamine hydrochloride is removed by filtration and the solvent is removed in vacuo leaving a black oil. The oil is extracted with several 200 ml portions of hot hexane. The extracts are allowed to stand whereupon a solid crystallizes. The solid is collected and is then recrystallized from hexane to give 21 g (29% yield) of the title compound as a tan solid melting at 84°-86° C.

Workup

  1. temperatureto cool to room temperature
  2. customDiphenylamine hydrochloride is removed by filtration
  3. customthe solvent is removed in vacuo
  4. customleaving a black oil
  5. extractionThe oil is extracted with several 200 ml portions of hot hexane
  6. customcrystallizes
  7. customThe solid is collected
  8. customis then recrystallized from hexane

Sources & evidence

ORD record
ord-e4e74eacadb04be59f140c0b9e5f9548
Source dataset
uspto-grants-1992_09
Patent number
US05151459

Reaction notes

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