Sodium Hydroxide → 1-(5-Chloro-3-phenoxypyridin-2-yl)thiourea

HRID 911763Notes

Reaction equation

HRID 911763 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[C:18]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][C:16]([Cl:26])=[CH:15][N:14]=1)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>C1COCC1>[Cl:26][C:16]1[CH:17]=[C:18]([O:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:13]([NH:12][C:10]([NH2:9])=[S:11])=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86631467HCID 86631467, compound

Product 1

HCID 866314681-(5-Chloro-3-phenoxypyridin-2-yl)thioureaYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A 250 mLround-bottomed flask was charged with 1-benzoyl-3-(5-chloro-3-phenoxypyridin-2-yl)thiourea (13.752 g, 35.826 mmol) and THF (100 mL). 3M NaOH (119.42 mL, 358.26 mmol) was added and the reaction mixture was heated to 90° C. for 18 hours. The reaction mixture was cooled to room temperature and concentrated. The resulting solids were filtered, washed with water, and dried to provide the title compound (9.49 g, 94.689% yield) as a yellow solid. 1H NMR (d6-DMSO) δ 9.97 (s, 1H), 9.25 (s, 1H), 8.87 (s, 1H), 8.11 (d, 1H), 7.49 (t, 2H), 7.31 (d, 1H), 7.28 (m, 2H), 7.23 (d, 2H); Mass spectrum (apci) m/z=279.9 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. filtrationThe resulting solids were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-cad57e804c374d4a852fb6c4430d76d3
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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