3,5-Dichlorophenyl isocyanate → HCID 23567544, compound

HRID 1797173Notes

Reaction equation

HRID 1797173 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[OH:6].[Cl:20][C:21]1[CH:22]=[C:23]([N:28]=[C:29]=[O:30])[CH:24]=[C:25]([Cl:27])[CH:26]=1>C(Cl)Cl>[CH3:19][N:2]([CH3:1])[CH2:3][CH2:4][CH:5]([O:6][C:29](=[O:30])[NH:28][C:23]1[CH:24]=[C:25]([Cl:27])[CH:26]=[C:21]([Cl:20])[CH:22]=1)[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 22177248HCID 22177248, compound

Product 1

HCID 23567544HCID 23567544, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-dimethylamino-1-(4-pyridin-4-yl-phenyl)-propan-1-ol (100 mg, 0.37 mmol) in CH2Cl2 (2 mL) was added 3,5-dichloro-phenylisocyanate (70 mg, 0.37 mmol) and the mixture was stirred at room temperature for 16 h. The mixture was concentrated to give a light brown oil, which was then purified by silica gel chromatography (5–10% MeOH/DCM gradient) to afford the title compound (3,5-dichloro-phenyl)-carbamic acid 3-dimethylamino-1-(4-pyridin-4-yl-phenyl)-propyl ester as a white solid, 131 mg (91%). 1H NMR (300 MHz, CD3OD): δ 8.77 (dd, 2H), 7.72 (d, 2H), 7.58 (m, 3H), 7.48 (d, 2H), 7.12 (t, 1H), 5.94 (t, 1H), 2.49 (m, 2H). 2.36 (s, 6H), 2.33 (m, 1H), 2.21 (m, 1H); MS(ESI): 444.1 (M+1), 446.1 (M+3).

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a light brown oil, which
  3. customwas then purified by silica gel chromatography (5–10% MeOH/DCM gradient)

Sources & evidence

ORD record
ord-9cff412c03f249898d99feebfcb1bdb4
Source dataset
uspto-grants-2006_04
Patent number
US07034056B2

Reaction notes

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