1-Isocyanato-4-methoxybenzene → HCID 117642838, compound

HRID 588752Notes

Reaction equation

HRID 588752 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([CH3:17])[S:8][C:6]=2[N:7]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=1>ClCCl.C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:19][CH2:20][N:21]([C:33]([NH:32][C:29]3[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=3)=[O:34])[CH2:22][CH2:23]2)[C:5]2[C:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[C:9]([CH3:17])[S:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 117642463HCID 117642463, compound

Product 1

HCID 117642838HCID 117642838, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 11 (50 mg, 0.16 mmol) in dichloromethane (2 mL) and acetonitrile (1 mL) was added 4-methoxyphenyl isocyanate (22 μL, 0.17 mmol). The reaction mixture was stirred overnight. The reaction mixture was evaporated in vacuo and the crude residue was purified by silica gel flash chromatography, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 1% to 2% methanol in dichloromethane), yielding the title compound (49 mg) as a white powder. 13C NMR δ (75 MHz, acetone-d6) 169.83, 161.99, 159.36, 155.05, 154.65, 135.58, 133.58, 130.55, 130.10 (2C), 127.84 (2C), 127.00, 126.13, 121.29 (2C), 113.26 (2C), 110.65, 64.94, 54.72 (2C), 49.33 (2C), 13.54. MS (m/z) 475 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe crude residue was purified by silica gel flash chromatography
  3. additiona mixture of methanol and dichloromethane (in a ratio

Sources & evidence

ORD record
ord-7a2e94091c8a434f886c8c124e4e3c83
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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