3,5-Dichlorophenyl isothiocyanate → HCID 54266822, compound

HRID 1387546Notes

Reaction equation

HRID 1387546 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]([O:14][CH3:15])=[CH:10][CH:9]=1)=[O:6].[Cl:21][C:22]1[CH:23]=[C:24]([N:29]=[C:30]=[S:31])[CH:25]=[C:26]([Cl:28])[CH:27]=1>C(OCC)(=O)C>[Cl:21][C:22]1[CH:23]=[C:24]([NH:29][C:30](=[S:31])[NH:1][C:2]2[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[C:5]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)=[O:6])[CH:25]=[C:26]([Cl:28])[CH:27]=1

Participants

4

Reactant 2

HCID 1387763,5-Dichlorophenyl isothiocyanateHCID 167904313-Amino-4-methoxy-N-(4-methoxyphenyl)-benzamide

Product 1

HCID 54266822HCID 54266822, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-amino-4-methoxy-N-(4-methoxyphenyl)-benzamide from Example 3 (0.681 g, 2.50 mmol) in ethyl acetate (80 mL) was heated briefly to 60° C. then filtered to clarity and mixed with 3,5-dichlorophenyl isothiocyanate (0.511 g, 2.50 mmol). The reaction was allowed to stand for 3 days at room temperature then concentrated to two-thirds volume and allowed to stand overnight. Filtration afforded the product (0.948 g); m.p 175-182° C.

Workup

  1. filtrationthen filtered to clarity
  2. concentrationthen concentrated to two-thirds volume
  3. waitto stand overnight
  4. filtrationFiltration

Sources & evidence

ORD record
ord-e39b79bf99724f158ec35ebabb9c6159
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Reaction notes

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