Methanol → HCID 178489420, compound

HRID 57290

Reaction equation

HRID 57290 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15](OC)=O.[NH2:23][NH2:24].[CH3:25]O>CC1C=CC(S(O)(=O)=O)=CC=1>[CH3:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]1[C:1]([C:2]2[S:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:25][NH:24][N:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 84462-MethylbenzothiazoleHCID 9321HydrazineHCID 61151Methyl 2-Methoxybenzoate

Product 1

HCID 178489420HCID 178489420, compound

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

The title compound (430 mg) was prepared in four steps starting from 1.49 g (10 mmol) of 2-methylbenzothiazole and 1.66 g (10 mmol) of methyl 2-methoxybenzoate. After the reaction with hydrazine, the addition product was dissolved in methanol and heated to reflux with a catalytic amount of p-TSA (15 mg) for 2 hours to yield the title compound. MS (m/z, ES+): 308 (M+1, 100%). Yield=14%.

Workup

  1. temperatureheated
  2. customto yield the title compound

Sources & evidence

ORD record
ord-d7164139c8c44f1997ebb671330a5343
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Linked notes

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