3,5-Dichlorophenyl isothiocyanate → HCID 54503944, compound

HRID 1859754Notes

Reaction equation

HRID 1859754 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])=[CH:5][C:4]=1[CH2:18][NH2:19].[Cl:20][C:21]1[CH:22]=[C:23]([N:28]=[C:29]=[S:30])[CH:24]=[C:25]([Cl:27])[CH:26]=1>C(N(CC)CC)C>[Cl:20][C:21]1[CH:22]=[C:23]([NH:28][C:29](=[S:30])[NH:19][CH2:18][C:4]2[CH:5]=[C:6]([CH:16]=[CH:17][C:3]=2[O:2][CH3:1])[C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[CH:24]=[C:25]([Cl:27])[CH:26]=1

Participants

4

Reactant 2

HCID 1387763,5-Dichlorophenyl isothiocyanateHCID 186262903-(Aminomethyl)-4-methoxy-N-phenylbenzamide

Product 1

HCID 54503944HCID 54503944, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of the product from Step C (0.1585 g, 0.54 mmol), triethylamine (0.5 mL) and 3,5-dichlorophenyl isothiocyanate (Lancaster) (0.138 g, 0.68 mmol) was heated briefly to 50° C. and then allowed to stand at room temperature over-night. The reaction mixture was then re-warmed to 50° C., filtered, and concentrated to an oil which was triturated in hexanes/ethyl acetate (2:1) and filtered through silica gel in ethyl acetate to afford the product (0.067 g); m.p. 208-210° C.

Workup

  1. waitto stand at room temperature over-night
  2. temperatureThe reaction mixture was then re-warmed to 50° C.
  3. filtrationfiltered
  4. concentrationconcentrated to an oil which
  5. customwas triturated in hexanes/ethyl acetate (2:1)
  6. filtrationfiltered through silica gel in ethyl acetate

Sources & evidence

ORD record
ord-6f09617074964f319b239b719cd37952
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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