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

HRID 1473992Notes

Reaction equation

HRID 1473992 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([O-])([O-])=O.[Cs+].[Cs+].[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27]Br.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][CH2:27][C:23]1[O:22][CH:26]=[CH:25][CH:24]=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 159560992-(2-Furylmethoxy)-4-(thiazol-2-ylamino)benzonitrileYield 57%

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 (105, 0.32 mmol) in acetone (4.4 mL) was treated with a freshly prepeared solution of 2-furylbromomethane in ether (0.60 mL, 0.32 mmol) at room temperature. Reaction control by TLC showed full conversion after 7.5 hrs. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 3/1) in 57% yield (54 mg).

Workup

  1. customReaction control by TLC
  2. customafter 7.5 hrs

Sources & evidence

ORD record
ord-40071d5bce274030b4984deaeb9b7956
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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