4-Methylphenyl isocyanate → HCID 71513652, compound

HRID 588753Notes

Reaction equation

HRID 588753 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][C:13]([NH2:23])=[N:14][C:15]=3[N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[S:10][N:9]=2)=[CH:4][CH:3]=1.[C:24]1([CH3:33])[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1>ClCCl>[NH2:23][C:13]1[N:12]=[C:11]2[S:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:16]2=[C:15]([N:17]2[CH2:18][CH2:19][N:20]([C:31]([NH:30][C:27]3[CH:28]=[CH:29][C:24]([CH3:33])=[CH:25][CH:26]=3)=[O:32])[CH2:21][CH2:22]2)[N:14]=1

Participants

4

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 117642421HCID 117642421, compound

Product 1

HCID 71513652HCID 71513652, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of Example 15 (0.2 mmol) in dichloromethane (5 mL) was added p-tolyl isocyanate (0.2 mmol). The reaction mixture was stirred at room temperature for 30 minutes. After concentration under reduced pressure, the residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio of 1:50), yielding the pure title compound (66 mg, 71%) as a yellowish solid. MS (m/z) 464.1 [M+H]+ (100%). δH (300 MHz, DMSO-d6, 25° C.) 8.36 (s, 1H, NH), 7.72 (dd, J 8.4, 5.6 Hz, 2H), 7.38 (t, J 8.7 Hz, 2H), 7.26 (d, J 8.4 Hz, 2H), 7.06 (s, 2H, NH2), 7.01 (d, J 8.4 Hz, 2H), 3.36 (br s, 4H), 3.17 (br s, 4H), 2.20 (s, 3H).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was purified by flash chromatography on silica
  3. additiona mixture of methanol and dichloromethane (in a ratio of 1:50),

Sources & evidence

ORD record
ord-4fe9372bd1a9426e8525acb8603bcf4d
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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