Potassium Carbonate → 2-((4-Fluoro-3-nitrophenoxy)methyl)benzo[d]thiazole

HRID 2178490Notes

Reaction equation

HRID 2178490 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]1[S:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:19][C:20]2[S:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3049782-(Chloromethyl)benzothiazoleHCID 167518614-Fluoro-3-nitrophenol

Product 1

HCID 904150262-((4-Fluoro-3-nitrophenoxy)methyl)benzo[d]thiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-fluoro-3-nitrophenol (2.1 g, 13 mmol), potassium carbonate (2.2 g, 16 mmol), 2-(chloromethyl)benzo[d]thiazole (2.4 g, 13 mmol) and DMF (15 mL) was stirred at 80° C. for 6 h. The reaction mixture was cooled to RT and poured onto ice water (300 mL). Solid precipitate was collected by vacuum filtration and dried in a vacuum oven at 60° C. to provide the title product, which was used without purification. MS (ESI): mass calcd. for C14H9FN2O3S, 304.1; m/z found, 305.1 [M+H]+. 1H-NMR (500 MHz, DMSO-d6) δ 8.15 (t, J=6.7, 1H), 8.08-8.01 (m, 1H), 7.90-7.84 (m, 1H), 7.63-7.53 (m, 3H), 7.52-7.45 (m, 1H), 5.75 (s, 2H).

Workup

  1. additionpoured onto ice water (300 mL)
  2. filtrationSolid precipitate was collected by vacuum filtration
  3. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-d90d26b9d7d44386903d04c681902c86
Source dataset
uspto-grants-2015_06
Patent number
US09067917B2

Reaction notes

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