4-Aminophenol → HCID 18794205, compound

HRID 1004039Notes

Reaction equation

HRID 1004039 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1>C(OC(O)C)C>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:2]2[N:7]=[C:6]([S:8][C:9]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 18327475213747-65-0

Product 1

HCID 18794205HCID 18794205, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 101298981-EthoxyethanolSolvent

Procedure

A mixture of 2-chloro-4-(4-methylphenylsulphanyl)pyrimidine (100 mg, 0.42 mmol) and 4-aminophenol (55 mg, 0.5 mmol) was heated at reflux in ethoxyethanol (2 ml) for 1.5 h. The reaction was concentrated under reduced pressure and subjected to column chromatography [silica, 20% ethyl acetate--CH2Cl2 ] to give the title compound (60 mg) as a buff solid m.p. 179-180°. δH (CDCl3) 8.01 (1H, d, J 5.4 Hz), 7.50-7.45 (2H, m), 7.31-7.27 (4H, m), 6.93 (1H, br s), 6.71-6.66 (2H, m), 6.25 (1H, d, J 5.4 Hz), 4.70 (1H, br s) and 2.44 (3H, s).

Workup

  1. temperaturewas heated
  2. concentrationThe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ccbae7a1f8154582b33316f679cae7be
Source dataset
uspto-grants-2000_04
Patent number
US06048866

Reaction notes

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