Water → HCID 135627611, compound

HRID 1699110Notes

Reaction equation

HRID 1699110 reaction equation
[N:1]1[N:2]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[OH2:17]>C(Cl)Cl>[N:1]1[N:2]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:12]3[C:11]([OH:17])=[C:10]([N:2]4[N:1]=[C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]5=[N:3]4)[CH:15]=[CH:14][CH:13]=3)[C:11]=2[OH:16])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 2

HCID 962WaterHCID 101982202-(2H-Benzotriazole-2-yl)phenol

Product 1

HCID 135627611HCID 135627611, compoundYield 519.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous ferric chloride (53.5 g, 0.33 mol) was added over a period of 180 minutes to a solution of 2-(2H-benzotriazol-2-yl)phenol, (20.0 g, 94.7 mmol), prepared by the method of Rosevear and Wilshire (Scheme I), Aust. J. Chem. 1985, 38, 1163-76, in methylene chloride (200 mL) and water (160 mg) at 0° C. After the addition was complete, the resulting mixture was removed from the cooling bath and stirred at room temperature for 36 hours. HPLC analysis of the reaction mixture (detector wavelength=290 nm) indicated 87 area % of product and 13 area % of starting material. The mixture was diluted with 2 L of methylene chloride and extracted with two 500 mL portions of 5% HCl, and two 1 L portions of water. The organic layer was rotary evaporated, leaving 19.4 g of a light grey solid which was 90% pure to HPLC. Surprisingly, very little or none of the para coupled product was found, as confirmed by NMR analysis. Recrystallization from o-dichlorobenzene gave COMPOUND 5 as off-white needles. 1H NMR (300 MHz, CD2Cl2) δ 11.62 (s, 2H), 8.41 (d, 2H), 7.88 (m, 4H), 7.42 (m, 4H), 7.39 (m, 2H), 7.10 (t, 2H).

Workup

  1. customprepared by the method of Rosevear and Wilshire (Scheme I), Aust
  2. customat 0° C
  3. additionAfter the addition
  4. customthe resulting mixture was removed from the cooling bath
  5. additionThe mixture was diluted with 2 L of methylene chloride
  6. extractionextracted with two 500 mL portions of 5% HCl, and two 1 L portions of water

Sources & evidence

ORD record
ord-74a26458b949427f87653d43839b6db2
Source dataset
uspto-grants-2002_02
Patent number
US06344505B1

Reaction notes

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