3,5-Dichlorophenyl isothiocyanate → HCID 10230282, compound

HRID 431390Notes

Reaction equation

HRID 431390 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)=[CH:4][C:3]=1[NH2:20].[Cl:21][C:22]1[CH:23]=[C:24]([N:29]=[C:30]=[S:31])[CH:25]=[C:26]([Cl:28])[CH:27]=1>ClCCl>[Cl:21][C:22]1[CH:23]=[C:24]([NH:29][C:30]([NH:20][C:3]2[CH:4]=[C:5]([O:8][CH2:9][C:10]3[C:11]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH:17]=[CH:18][CH:19]=3)[CH:6]=[CH:7][C:2]=2[Br:1])=[S:31])[CH:25]=[C:26]([Cl:28])[CH:27]=1

Participants

4

Reactant 2

HCID 1387763,5-Dichlorophenyl isothiocyanateHCID 18763448HCID 18763448, compound

Product 1

HCID 10230282HCID 10230282, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-bromo-5-(2-naphthylmethoxy)phenylamine (100 mg, 0.3 mmol) and 3,5-dichlorophenylisothiocyanate (60 mg, 0.3 mmol) in 10 mL of dichloromethane was stirred at room temperature for 16 h. The reaction mixture was evaporated to dryness and the residue recrystallized from ethyl acetate/hexane to give 60 mg of product in (38%) yield as a white solid: mp 149-151° C. 1H NMR (400 MHz, Me2SO-d6) δ5.56 (s, 2H); 7.02 (dd, 1H, J=3.0, 8.9); 7.29 (d, 1H, J=3.0); 7.35 (t, 1H, J=1.8); 7.49-7.69 (m, 7H); 7.93-7.99 (m, 2H); 8.07-8.10 (m, 1H); 9.78 (s, 1H); 10.10 (s, 1H). Anal. Calcd for C24H17BrCl2N2OS: C, 54.16; H, 3.22; N, 5.26; S, 6.02; Cl, 13.32; Br, 15.01. Found: C, 54.17; H, 3.32; N, 5.28; S,6.10; Cl, 13.31; Br, 15.00.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-945dd496b5ff4ae081a150eb3ccf5820
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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