Methanol → HCID 14366096, compound

HRID 1383047Notes

Reaction equation

HRID 1383047 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[N:11]=[C:12]=[O:13].CCCCC(C(O[Sn](O[C:34](C(CCCC)CC)=[O:35])(CCCC)CCCC)=O)CC.[CH3:43][N:44]([CH3:49])[C:45]([S:47][NH2:48])=[S:46].CO>C1(C)C=CC=CC=1>[CH3:43][N:44]([CH3:49])[C:45]([S:47][NH:48][C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:11][C:12]([O:35][CH3:34])=[O:13])[CH:4]=1)=[O:10])=[S:46]

Participants

6

Reactant 4

HCID 887MethanolHCID 11443Toluene 2,4-DiisocyanateHCID 13658362(Aminosulfanyl)(dimethylamino)methanethioneHCID 16682803Dibutyltin bis(2-ethylhexanoate)

Product 1

HCID 14366096HCID 14366096, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
75 °C

Procedure

Toluene-2,4-diisocyanate (17.9 grams, 0.10 mole) and dibutyltin di-2-ethylhexanoate (0.20 grams) were dissolved in toluene (100 ml). The solution was heated to 75° C., and a solution of S-(dimethylthiocarbamyl)sulfenamide (13.6 grams, 0.10 mole) in toluene (200 ml) was slowly added, with constant stirring, over a period of 45 minutes. When the addition was complete, the mixture was maintained at 70° C.-80° C. and stirred for an additional hour. Then anhydrous methanol (15 ml) was added. The slurry was cooled to room temperature and filtered. The white powdery product was dried at 60° C. Yield 30.5 grams, melting point 180°-185° C. IR and NMR spectra were consistent with the assigned structure.

Workup

  1. additionWhen the addition
  2. temperaturethe mixture was maintained at 70° C.-80° C.
  3. temperatureThe slurry was cooled to room temperature
  4. filtrationfiltered
  5. customThe white powdery product was dried at 60° C

Sources & evidence

ORD record
ord-448a922196c9412b9c85f754d3d084ab
Source dataset
uspto-grants-1989_02
Patent number
US04808714

Reaction notes

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