Dichloromethane → HCID 19702671, compound

HRID 1376701Notes

Reaction equation

HRID 1376701 reaction equation
[CH2:1]([N:4]([CH2:14][CH2:15][OH:16])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C(N(CC)CC)C.ClCCl.[C:27](Cl)(=[O:31])[C:28]([CH3:30])=[CH2:29]>C(OCC)C>[CH2:1]([N:4]([CH2:14][CH2:15][O:16][C:27](=[O:31])[C:28]([CH3:30])=[CH2:29])[C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471Triethylamine2×HCID 13528Methacryloyl chloride2×HCID 19702699HCID 19702699, compound

Product 1

HCID 19702671HCID 19702671, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of N-allyl-N-(2-hydroxyethyl)-4-nitrobenzenamine (2.22 g, 0.01 mol), triethylamine (1.2 ml) and dichloromethane (20 ml) is added methacryloyl chloride (1.14 g, 11 mmol) with stirring at room temperature. After 3 hours, an additional amount of triethylamine (0.6 ml) and methacryloyl chloride (0.5 g) is added and stirring continued for 3 hours. The mixture is diluted with ethyl ether (100 ml) and washed with water two times, washed with brine, and dried over sodium sulfate. The mixture is concentrated and chromatographed on silica with hexane-ethyl acetate to provide N-allyl-N-(2-methacryloyloxyethyl)-4-nitrobenzenamine.

Workup

  1. stirringstirring
  2. waitcontinued for 3 hours
  3. washwashed with water two times
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe mixture is concentrated
  7. customchromatographed on silica with hexane-ethyl acetate

Sources & evidence

ORD record
ord-90c78f499557416896ebb38b3a6e0a46
Source dataset
uspto-grants-1997_09
Patent number
US05663308

Reaction notes

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