3-Amino-4-methoxybenzanilide → HCID 54150752, compound

HRID 1859697Notes

Reaction equation

HRID 1859697 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].[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[S:28])=[CH:22][CH:21]=1>C(OCC)(=O)C>[F:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[S:28])[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:22][CH:21]=1

Participants

4

Reactant 2

HCID 84263-Amino-4-methoxybenzanilideHCID 152414-Fluorophenyl isothiocyanate

Product 1

HCID 54150752HCID 54150752, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-amino-4-methoxybenzanilide (0.973 g, 4.00 mmol) in ethyl acetate (75 mL) was heated briefly to ˜60° C. The mixture was filtered to clarity and 4-fluorophenyl isothiocyanate (0.49 mL, 4.04 mmol) was added to the filtrate. After 3 days, the mixture was concentrated until a crystalline precipitate was obtained, then allowed to stand several hours at room temperature. Filtration followed by trituration of the collected solid in ether afforded the product (0.4949 g); m.p. 182-183° C.

Workup

  1. additionwas added to the filtrate
  2. concentrationthe mixture was concentrated until a crystalline precipitate
  3. customwas obtained
  4. waitto stand several hours at room temperature
  5. filtrationFiltration

Sources & evidence

ORD record
ord-f147c1960d714178979c9bce49f994f8
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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