3-Amino-4-methoxybenzanilide → HCID 53855612, compound

HRID 1859683Notes

Reaction equation

HRID 1859683 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].[Cl:19][C:20]1[CH:21]=[C:22]([N:27]=[C:28]=[S:29])[CH:23]=[C:24]([Cl:26])[CH:25]=1>C(OCC)(=O)C>[Cl:19][C:20]1[CH:21]=[C:22]([NH:27][C:28](=[S:29])[NH:1][C:2]2[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:6])[CH:23]=[C:24]([Cl:26])[CH:25]=1

Participants

4

Reactant 2

HCID 84263-Amino-4-methoxybenzanilideHCID 1387763,5-Dichlorophenyl isothiocyanate

Product 1

HCID 53855612HCID 53855612, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-amino-4-methoxy-N-phenyl-benzamide (0.277 g, 1.14 mmol) and 3,5-dichlorophenyl isothiocyanate (0.238 g, 1.17 mmol) in ethyl acetate (30 mL) was warmed until a solution was obtained, then allowed to stand at room temperature for 3 days. The reaction was concentrated until a crystalline precipitate was obtained then allowed to stand overnight at room temperature. The solid was collected by filtration, rinsed with ethyl acetate/hexane, and dried to afford the product (0.423 g); m.p. 195-197° C.

Workup

  1. temperaturewas warmed until a solution
  2. customwas obtained
  3. concentrationThe reaction was concentrated until a crystalline precipitate
  4. customwas obtained
  5. waitto stand overnight at room temperature
  6. filtrationThe solid was collected by filtration
  7. washrinsed with ethyl acetate/hexane
  8. customdried

Sources & evidence

ORD record
ord-e694f00b07c24c53a3f71ba04794e040
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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