Water → HCID 59295488, compound

HRID 2233312Notes

Reaction equation

HRID 2233312 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].[Br:13][C:14]1[S:15][C:16]([CH2:20]OS(C)(=O)=O)=[C:17]([CH3:19])[N:18]=1.O>CN(C)C=O.C(OCC)(=O)C>[Br:13][C:14]1[S:15][C:16]([CH2:20][O:10][C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[CH:9]=2)=[C:17]([CH3:19])[N:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 592955205-Thiazolemethanol, 2-bromo-4-methyl-, 5-methanesulfonate

Product 1

HCID 59295488HCID 59295488, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-Chloro-4-hydroxy-benzonitrile (1.6 g, 10.1 mmol) in dry dimethylformamide (30 mL) is carefully added sodium hydride (486 mg, 12.1 mmol). The resulting mixture is stirred for 20 minutes at room temperature. A solution of Methanesulfonic acid 2-bromo-4-methyl-thiazol-5-ylmethyl ester (3.0 g, 10.1 mmol) in dry dimethylformamide (5 mL) is added and the reaction mixture is stirred at room temperature. The reaction mixture is diluted with 100 mL of ethyl acetate after 5 h and water (20 mL) is carefully added (Caution: development of H2). The phases are separated and the organic phase is dried over MgSO4. The solvent is removed under reduced pressure and the crude product is purified by reversed phase HPLC to yield 2.2 g of 4-(2-Bromo-4-methyl-thiazol-5-ylmethoxy)-2-chloro-benzonitrile. C12H8BrClN2OS (343.63), MS (ESI): 343.0 (M+H+).

Workup

  1. stirringthe reaction mixture is stirred at room temperature
  2. customThe phases are separated
  3. dry with materialthe organic phase is dried over MgSO4
  4. customThe solvent is removed under reduced pressure
  5. customthe crude product is purified by reversed phase HPLC

Sources & evidence

ORD record
ord-c262ef7203474863a7969a5f6877620a
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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