3-Methoxy-4-nitrobenzoic acid → 2-(3-Methoxy-4-nitrophenyl)-6-methoxybenzothiazole

HRID 339494

Reaction equation

HRID 339494 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[SH:10].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[C:16](O)=O>C(Cl)Cl>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:16]2[S:10][C:3]3[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=3[N:1]=2)[CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 787643-Methoxy-4-nitrobenzoic acidHCID 2355092-Amino-5-methoxybenzene-1-thiol

Product 1

HCID 672368252-(3-Methoxy-4-nitrophenyl)-6-methoxybenzothiazoleYield 32.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A thoroughly mixed paste of 2-amino-5-methoxybenzenethiol (2.0 g, 12.88 mmol) and 3-methoxy-4-nitrobenzoic acid (2.54 g, 12.88 mmol) in trimethylsilylpolyphosphate (10 ml) was stirred and heated at 150° C. under an atmosphere of argon for 2 h. On cooling to room temperature, the reaction mixture was suspended in DCM (300 ml) and adsorbed onto flash silica and initially purified using a plug of flash silica eluting with DCM, then DCM/EtOAc (6:1). Further purification of the collected fractions by flash chromatography (20:1 DCM/Hexane) gave the title compound (1.32 g, 32%) as a yellow solid.

Workup

  1. temperatureOn cooling to room temperature
  2. custominitially purified
  3. customFurther purification of the collected fractions by flash chromatography (20:1 DCM/Hexane)

Sources & evidence

ORD record
ord-24ac5bbdb6bc427390a80992ca7520f5
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Linked notes

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