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

HRID 462479Notes

Reaction equation

HRID 462479 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 product 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-5b2fc316f8214265894e582d4f54d27f
Source dataset
uspto-grants-1985_05
Patent number
US04515813

Reaction notes

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