Diethyl Ether → 2-(3-Furylmethoxy)-4-(thiazol-2-ylamino)benzonitrile

HRID 1473995Notes

Reaction equation

HRID 1473995 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:16]([O-])([O-])=O.[Cs+].[Cs+].[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1CBr.CCOCC>CC(C)=O>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:9][C:2]=1[O:1][CH2:16][C:24]1[CH:25]=[CH:26][O:22][CH:23]=1)#[N:5]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 46037652-(Bromomethyl)furanHCID 860960092-Hydroxy-4-(thiazol-2-ylamino)benzonitrile

Product 1

HCID 159561012-(3-Furylmethoxy)-4-(thiazol-2-ylamino)benzonitrileYield 11%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation, Method B, a mixture of 2-hydroxy-4-(thiazol-2-ylamino)benzonitrile (70 mg, 0.32 mmol) and Cs2CO3 (0.32 mmol) in acetone (4.4 mL) was treated with a freshly prepeared solution of 2-furylbromomethane in ether (71 mg, 0.32 mmol) at RT. Reaction control by TLC showed full conversion after 2 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 65/35) in 11% yield (10 mg).

Workup

  1. customReaction control by TLC
  2. customafter 2 h

Sources & evidence

ORD record
ord-a3ca7a095e2543fc8ff4f67dcbd72493
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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