Diphenylmethane diisocyanate → HCID 87586011, compound

HRID 732845Notes

Reaction equation

HRID 732845 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8](=[O:17])[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].[CH:18]1[C:23]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=2)=[CH:22][CH:21]=[C:20]([N:34]=[C:35]=[O:36])[CH:19]=1>C1(C)C=CC=CC=1>[N:31]([C:28]1[CH:29]=[CH:30][C:25]([CH2:24][C:23]2[CH:18]=[CH:19][C:20]([NH:34][C:35]([O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8](=[O:17])[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:10])=[O:36])=[CH:21][CH:22]=2)=[CH:26][CH:27]=1)=[C:32]=[O:33]

Participants

4

Reactant 2

HCID 7570Diphenylmethane diisocyanateHCID 12187661Benzeneacetic acid, .alpha.-oxo-, 2-(2-hydroxyethoxy)ethyl ester

Product 1

HCID 87586011HCID 87586011, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Under argon gas, 2.14 g of the phenylglyoxylic acid (2-hydroxyethoxy)ethyl ester from Example 1 and 2.24 g of 4,4′-diphenylmethane diisocyanate (Desmodur VL, Bayer) in 15 g of toluene are placed as the initial charge in a 50 ml multi-necked flask and refluxed at 110° C. After 19 hours, the solution is cooled and the toluene is concentrated using a rotary evaporator. The residue is dried under a high vacuum for two hours. 4.6 g of a viscous, slightly brownish oil are obtained. The conversion and the composition of the product mixture are verified by 1H-NMR spectrum and IR spectrum (NCO bands).

Workup

  1. additioninitial charge in a 50 ml multi-necked flask
  2. temperaturethe solution is cooled
  3. concentrationthe toluene is concentrated
  4. customa rotary evaporator
  5. customThe residue is dried under a high vacuum for two hours
  6. custom4.6 g of a viscous, slightly brownish oil are obtained

Sources & evidence

ORD record
ord-610eb39ac72a4cc180c23b606ef74eb1
Source dataset
uspto-grants-2009_09
Patent number
US07588880B2

Reaction notes

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