Water → HCID 18763414, compound

HRID 431391Notes

Reaction equation

HRID 431391 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[CH:12]=[C:13]([NH2:19])[CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:20][C:21]1[CH:22]=[C:23]([N:28]=[C:29]=S)[CH:24]=[C:25]([Cl:27])[CH:26]=1.[OH2:31]>ClCCl>[Cl:20][C:21]1[CH:22]=[C:23]([NH:28][C:29]([NH:19][C:13]2[CH:14]=[CH:15][C:16]([O:17][CH3:18])=[C:11]([O:10][CH2:9][C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)[CH:12]=2)=[O:31])[CH:24]=[C:25]([Cl:27])[CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1387763,5-Dichlorophenyl isothiocyanateHCID 18763421HCID 18763421, compound

Product 1

HCID 18763414HCID 18763414, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-[(3,5-dichlorophenyl)methoxy]-4-methoxyphenylamine (0.596 g, 2 mmol) in dichloromethane (30 mL) was added 3,5-dichlorophenylisothiocyanate (0.408 g, 2 mmol) in one portion. Stirring was continued overnight. Water (100 mL) was added to the mixture, and after extraction and separation of organic layer the solvent was evaporated in vacuo to give a solid, which was triturated with a mixture diethyl ether:hexanes and filtered. Yield 0.273 g (27%). White micro-crystals, m.p. 154-155° C. (dec.); 1H NMR (DMSO-d6, 400 MHz) 9.67 (s, 1H); 9.74 (s, 1H); 7.59 (s, 2H); 7.53 (s, 1H); 7.48 (s, 2H); 7.30 (s, 1H); 7.11 (s, 1H); 7.00 (d, J=8.5 Hz, 1H), 6.92 (dd, J=9.0 and 2.5 Hz, 1H); 5.10 (s, 2H); 3.79 (s, 3H). Anal: Calcd for: C, 50.22; H, 3.21; N, 5.58. Found: C, 50.50; H, 3.45; N, 5.56.

Workup

  1. extractionafter extraction and separation of organic layer the solvent
  2. customwas evaporated in vacuo
  3. customto give a solid, which
  4. customwas triturated with a mixture diethyl ether
  5. filtrationhexanes and filtered

Sources & evidence

ORD record
ord-d963d03a7eb843e5938e7caf1b9d4add
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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