1-Isocyanato-4-methoxybenzene → HCID 117642729, compound

HRID 588755Notes

Reaction equation

HRID 588755 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:5]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1>ClCCl.C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([C:31]([NH:30][C:27]3[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)=[O:32])[CH2:18][CH2:17]2)[C:5]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][S:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 117642607HCID 117642607, compound

Product 1

HCID 117642729HCID 117642729, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 20 (70 mg, 0.23 mmol) in dichloromethane (2 mL) and acetonitrile (2 mL) was added 4-methoxyphenyl isocyanate (31 μL, 0.24 mmol). The reaction mixture was stirred overnight. The solvents were evaporated in vacuo and the crude residue was purified by flash chromatography, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually increasing from 1% to 3% methanol in dichloromethane), yielding the title compound (61 mg) as a white powder. 13C NMR δ (75 MHz, CD3OD) 171.65, 162.60, 160.54, 159.64, 155.32, 154.73, 133.60, 127.71, 124.13, 121.41 (2C), 113.30 (2C), 106.19, 60.79, 54.73, 47.93 (2C), 43.38 (2C), 13.73. MS (m/z) 457 [M+H]+.

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe crude residue was purified by flash chromatography
  3. additiona mixture of methanol and dichloromethane (in a ratio
  4. temperaturegradually increasing from 1% to 3% methanol in dichloromethane),

Sources & evidence

ORD record
ord-06d5937b00b84181873b29e9074cd2a1
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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