m-Tolylisothiocyanate → N-(3,4-Dimethylphenyl)-4-methoxy-3-(3-m-tolyl-thioureido)-benzamide

HRID 1859717Notes

Reaction equation

HRID 1859717 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=1)=[O:6].[CH3:21][C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[S:30])[CH:25]=[CH:26][CH:27]=1>C(OCC)(=O)C>[CH3:15][C:10]1[CH:9]=[C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:2]([NH:1][C:29]([NH:28][C:24]3[CH:23]=[C:22]([CH3:21])[CH:27]=[CH:26][CH:25]=3)=[S:30])[CH:3]=2)[CH:13]=[CH:12][C:11]=1[CH3:14]

Participants

4

Reactant 2

HCID 69304m-TolylisothiocyanateHCID 167860273-Amino-4-methoxy-N-(3,4-dimethylphenyl)-benzamide

Product 1

HCID 54106240N-(3,4-Dimethylphenyl)-4-methoxy-3-(3-m-tolyl-thioureido)-benzamideYield 52.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-amino-N-(3,4-dimethylphenyl)-4-methoxy-benzamide from Example 6 (0.541 g, 2.00 mmol) and 3-methylphenyl isothiocyanate (0.28 mL, 2.07 mmol) in ethyl acetate (35 mL) was boiled until nearly all the solvent had evaporated. Filtration after 2 days at room temperature afforded the product (0.44 g) in two crops; m.p. 155-160° C.

Workup

  1. customhad evaporated
  2. filtrationFiltration after 2 days at room temperature

Sources & evidence

ORD record
ord-fe5c534287ad45aa9807dc5193f89104
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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