3,5-Dichlorophenyl isothiocyanate → N-(4-Chlorophenyl)-3-[3-(3,5-dichlorophenyl)-thioureido]-4-methoxy-benzamide

HRID 1387555Notes

Reaction equation

HRID 1387555 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:6].[Cl:20][C:21]1[CH:22]=[C:23]([N:28]=[C:29]=[S:30])[CH:24]=[C:25]([Cl:27])[CH:26]=1>CN(C=O)C.O>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:2]([NH:1][C:29]([NH:28][C:23]3[CH:24]=[C:25]([Cl:27])[CH:26]=[C:21]([Cl:20])[CH:22]=3)=[S:30])[CH:3]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 1387763,5-Dichlorophenyl isothiocyanateHCID 167929923-Amino-4-methoxy-N-(4-chlorophenyl)-benzamide

Product 1

HCID 17921770N-(4-Chlorophenyl)-3-[3-(3,5-dichlorophenyl)-thioureido]-4-methoxy-benzamideYield 61.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-amino-N-(4-chlorophenyl)-4-methoxy-benzamide from Example 2 (1.113 g, 4.02 mmol) and 3,5-dichlorophenyl isothiocyanate (0.820 g, 4.02 mmol) in DMF (10 mL) was allowed to stand at room temperature overnight. The mixture was then diluted with 50 mL H2O and the precipitate collected by filtration and dried. Trituration in first ether then ethyl acetate followed by filtration afforded the product (1.19 g); m.p. 180-185° C.

Workup

  1. filtrationthe precipitate collected by filtration
  2. customdried
  3. filtrationTrituration in first ether then ethyl acetate followed by filtration

Sources & evidence

ORD record
ord-19e4474bef38477fa2eb94b9aa6b52cc
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Reaction notes

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