m-Tolyl isocyanate → HCID 71513436, compound

HRID 588750Notes

Reaction equation

HRID 588750 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][C:14]([F:17])=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1.[C:24]1([CH3:33])[CH:29]=[CH:28][CH:27]=[C:26]([N:30]=[C:31]=[O:32])[CH:25]=1>O1CCOCC1.ClCCl>[NH2:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][N:21]([C:31]([NH:30][C:26]3[CH:25]=[C:24]([CH3:33])[CH:29]=[CH:28][CH:27]=3)=[O:32])[CH2:20][CH2:19]2)[C:5]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)=[CH:9][S:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 71492232HCID 71492232, compound

Product 1

HCID 71513436HCID 71513436, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of Example 1 (115 mg, 0.35 mmol) in 1,4-dioxane (15 mL) was added m-tolyl isocyanate (0.38 mmol). The reaction mixture was stirred overnight. The reaction mixture was diluted with dichloromethane and the organic layer was extracted several times with water. The combined organic layers were 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 0.5% to 1% methanol in dichloromethane), yielding the title compound as a white powder. MS (m/z) 463 [M+H]+.

Workup

  1. extractionthe organic layer was extracted several times with water
  2. customThe combined organic layers were evaporated in vacuo
  3. customthe crude residue was purified by silica gel flash chromatography
  4. additiona mixture of methanol and dichloromethane (in a ratio

Sources & evidence

ORD record
ord-1e777eda1dcb4f88881ad07540f9a362
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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