1,1-Dichloroethane → 1-(4-Chloro-phenyl)-3-[4-hydroxy-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-urea

HRID 1362955Notes

Reaction equation

HRID 1362955 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[O:17])[CH:10]=[CH:11][C:12]=2[O:13]C)=[CH:5][CH:4]=[N:3]1.ClC(Cl)C.BrB(Br)Br>O>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH:15][C:16]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)=[O:17])[CH:10]=[CH:11][C:12]=2[OH:13])=[CH:5][CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 25134Boron tribromideHCID 117101541-(4-Chloro-phenyl)3-[4-methoxy-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-urea

Product 1

HCID 1356979361-(4-Chloro-phenyl)-3-[4-hydroxy-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-[3-(2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(4-chloro-phenyl)-urea (6.35 g, 17.8 mmol) and dichloroethane (500 Lm), tribromoborane (10 mL, 106 mmol) was added. The mixture was allowed to warm to room temperature. After stirring over the weekend, the mixture was cooled in an ice bath and a mixture of ice cold ammonium hydroxide and water (ca. 100 mL) was added slowly. The mixture was transferred into a separatory funnel and extracted with methylene chloride and water. Solid in the water phase was filtered off and washed with water to give 1-[3-(2-methyl-2H-pyrazol-3-yl)-4-hydroxy-phenyl]-3-(4-chloro-phenyl)-urea as a white solid (4.92 g, 90% pure, 12.7 mmol, 71%). Combined organic phases were dried over MgSO4, filtered, and concentrated to afford additional 1-[3-(2-methyl-2H-pyrazol-3-yl)-4-hydroxy-phenyl]-3-(4-chloro-phenyl)-urea as a white solid (1.71 g, 4.99 mmol, 28%). Overall yield: 99%. LCMS m/z (%)=343.1 (M+H). 1H NMR (400 MHz, CDCl3) δ: 9.60 (br s, 1H), 8.78 (s, 1H), 8.53 (s, 1H), 7.48-7.42 (m, 31), 7.32-7.27 (m, 4H), 6.91-6.89 (m, 1H), 6.21 (d, J=1.8 Hz, 1H), 3.68 (s, 3H).

Workup

  1. additionwas added
  2. temperaturethe mixture was cooled in an ice bath
  3. additionwas added slowly
  4. customThe mixture was transferred into a separatory funnel
  5. extractionextracted with methylene chloride and water
  6. filtrationSolid in the water phase was filtered off
  7. washwashed with water

Sources & evidence

ORD record
ord-e84f2d6b816c462d8059951cfd3b8a90
Source dataset
uspto-grants-2011_02
Patent number
US07884101B2

Reaction notes

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