4-(Dimethylamino)phenyl isocyanate → HCID 117642503, compound

HRID 588756Notes

Reaction equation

HRID 588756 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:5]2[C:10]([CH3:11])=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:18][N:19]([CH3:29])[C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1>ClCCl.C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:13][CH2:14][N:15]([C:27]([NH:26][C:23]3[CH:24]=[CH:25][C:20]([N:19]([CH3:29])[CH3:18])=[CH:21][CH:22]=3)=[O:28])[CH2:16][CH2:17]2)[C:5]2[C:10]([CH3:11])=[CH:9][S:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 27333724-(Dimethylamino)phenyl isocyanateHCID 117642828HCID 117642828, compound

Product 1

HCID 117642503HCID 117642503, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 22 (70 mg, 0.28 mmol) in dichloromethane (2 mL) and acetonitrile (2 mL) was added 4-(dimethylamino)phenyl isocyanate (48 mg, 0.29 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 4% methanol in dichloromethane), yielding the title compound (75 mg) as a white powder. 13C NMR δ (75 MHz, CDCl3) 171.76, 164.09, 158.58, 155.98, 147.34, 129.12, 128.44, 122.79 (2C), 114.11 (2C), 113.95, 113.07, 49.96 (2C), 43.42 (2C), 40.79 (2C), 16.75. MS (m/z) 412 [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 4% methanol in dichloromethane),

Sources & evidence

ORD record
ord-7d080b7ac3ca45ba9049cf26a458e4f4
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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