Toluene 2,4-Diisocyanate → 1-phenyl-3-n-heptyl-2-S-ethyl isothiourea toluene-2,4-diisocyanate

HRID 2198465Notes

Reaction equation

HRID 2198465 reaction equation
[C:1]1([NH:7][C:8](=[N:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[S:9][CH2:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][C:22]=1[N:30]=[C:31]=[O:32].[N-]=C=O>O1CCCC1.NC(=N)S>[C:1]1([NH:7][C:8](=[N:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[S:9][CH2:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][C:22]=1[N:30]=[C:31]=[O:32]

Participants

6

Reactant 3

HCID 11443Toluene 2,4-DiisocyanateHCID 105034IsocyanateHCID 203985051-phenyl-3-n-heptyl-2-S-ethyl isothiourea

Product 1

HCID 1317128601-phenyl-3-n-heptyl-2-S-ethyl isothiourea toluene-2,4-diisocyanate

Reagents, catalysts & solvents 2

HCID 178513445HCID 178513445, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The equipment was the same as used in Example 26. 2.78 g (0.01 mole) 1-phenyl-3-n-heptyl-2-S-ethyl isothiourea in 35 ml of tetrahydrofuran were mixed with 0.87 g (0.005 mole) toluene-2,4-diisocyanate. The reaction mixture was then refluxed on a steam bath for 1 hour, then 15 drops of the isothiourea was added, and the reaction mixture was refluxed for an additional hour to react all the isocyanate. The reaction mixture was vacuum evaporated to produce 4.1 g of a viscous, yellow liquid having a nD30 of 1.5737. The produce was identified as the title product by IR and NMR spectra analyses. Compound No. 151 in Table I.

Workup

  1. temperatureThe reaction mixture was then refluxed on a steam bath for 1 hour
  2. temperaturethe reaction mixture was refluxed for an additional hour
  3. customevaporated
  4. customto produce 4.1 g of a viscous, yellow liquid

Sources & evidence

ORD record
ord-b49e52cc29a44874bd9cce04ac47b06a
Source dataset
uspto-grants-1982_11
Patent number
US04357351

Reaction notes

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