Water → HCID 178490664, compound

HRID 254667Notes

Reaction equation

HRID 254667 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:25][C:26]1[N:27]=[C:28]([CH3:31])[S:29][CH:30]=1.O>CN(C)C=O>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[N:7]([CH2:25][C:26]2[N:27]=[C:28]([CH3:31])[S:29][CH:30]=2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 7363414-(Chloromethyl)-2-methyl-1,3-thiazoleHCID 87094486n-(5-Tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

Product 1

HCID 178490664HCID 178490664, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 74B (0.79 g, 2.43 mmol) in N,N-dimethylformamide (20 mL) was added sodium hydride (Aldrich, 98 mg, 2.43 mmol) and the reaction mixture was stirred for 15 min and 4-(chloromethyl)-2-methylthiazole (0.36 g, 2.43 mmol) was added. The reaction mixture was stirred at room temperature for 18 hr, poured into water (75 mL) and then extracted with EtOAc (75 mL). The organic layer was washed with water (2×75 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to provide the title compound. MS, DCI, m/z 436 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hr
  2. extractionextracted with EtOAc (75 mL)
  3. washThe organic layer was washed with water (2×75 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-48ce000ad0644a088829aeda7e6cc712
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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