Diethyl Ether → N-(3-(Furan-3-ylmethoxy)-4-methylphenyl)thiazol-2-amine

HRID 1473993Notes

Reaction equation

HRID 1473993 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:4][C:3]=1[OH:14].[C:15]([O-])([O-])=O.[Cs+].[Cs+].[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1CBr.CCOCC>CC(C)=O>[O:21]1[CH:25]=[CH:24][C:23]([CH2:15][O:14][C:3]2[CH:4]=[C:5]([NH:8][C:9]3[S:10][CH:11]=[CH:12][N:13]=3)[CH:6]=[CH:7][C:2]=2[CH3:1])=[CH:22]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 46037652-(Bromomethyl)furan2×HCID 866450292-Methyl-5-(thiazol-2-ylamino)phenol

Product 1

HCID 86645042N-(3-(Furan-3-ylmethoxy)-4-methylphenyl)thiazol-2-amineYield 54%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation, Method B, a mixture of 2-methyl-5-(thiazol-2-ylamino)phenol (100 mg, 0.48 mmol) and Cs2CO3 (0.48 mmol) in acetone (4.4 mL) was treated with a freshly prepeared solution of 2-furylbromomethane in ether (0.53 mmol) at 0°. After 30 min the reaction was heated to RT. After 4 h, another 2-furylbromomethane (35 mg) were added and stirred for another 1.5 h. Reaction control by TLC showed full conversion after 6 h 40 min. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 3/1) in 54% yield (75 mg).

Workup

  1. customReaction control by TLC
  2. customafter 6 h
  3. custom40 min

Sources & evidence

ORD record
ord-574d7c37ea5e4f518fb933fb40857c8c
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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