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

HRID 1859709Notes

Reaction equation

HRID 1859709 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-b6be09944ced48b89c64cdcbad88bd8c
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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