Dichloromethane → 2-(2-Methoxy-4-nitrophenyl)benzothiazole

HRID 339495Notes

Reaction equation

HRID 339495 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[CH3:9][O:10][C:11]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:12]=1[C:13](O)=O.C(Cl)Cl>CCOCC>[CH3:9][O:10][C:11]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:12]=1[C:13]1[S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 87132-AminothiophenolHCID 757764-Nitro-o-anisic acid

Product 1

HCID 672372802-(2-Methoxy-4-nitrophenyl)benzothiazoleYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
150 °C

Procedure

A thoroughly mixed paste of 2-aminobenzenethiol (0.63 g, 5.07 mmol) and 2-methoxy-4-nitrobenzoic acid (1.0 g, 5.07 mmol) in trimethylsilylpolyphosphate (5 ml) was stirred and heated at 150° C. under an atmosphere of argon for 1.5 h. On cooling to room temperature the reaction mixture was a solid mass to which was added DCM (35 ml) and Et2O (50 ml). The solid was broken up and collected by filtration, then recrystallised from AcOH and dried under high vacuum for 18 h to give the title compound (0.90 g, 62%) as a yellow solid.

Workup

  1. temperatureOn cooling to room temperature the reaction mixture
  2. filtrationcollected by filtration
  3. customrecrystallised from AcOH
  4. customdried under high vacuum for 18 h

Sources & evidence

ORD record
ord-a24f807588bb43c18473164e23930830
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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