Carbon Disulfide → (2-Isothiocyanatopropan-2-yl)benzene

HRID 634220Notes

Reaction equation

HRID 634220 reaction equation
[C:1]([NH2:10])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].CCN(CC)CC.[C:18](=S)=[S:19].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1COCC1>[N:10]([C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2])=[C:18]=[S:19]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 68509Cumylamine

Product 1

HCID 12376018(2-Isothiocyanatopropan-2-yl)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Cumylamine (5.32 mL, 37.0 mmol) (TCI America) and Et3N (16.97 mL, 122 mmol) (Aldrich) were mixed in THF (40 mL) at 0° C. under a nitrogen atmosphere. Carbon disulfide (2.224 mL, 37.0 mmol) (J.T.Baker) was added dropwise via syringe over the course of 10 min. The reaction was stirred at 0° C. for 1 h before being warmed to RT and stirred for 1 h. p-Toluenesulfonyl chloride (7.76 g, 40.7 mmol) (Fluka) was added, and the reaction was stirred at RT for 1 h. The mixture was quenched with 1 M HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated to give (2-isothiocyanatopropan-2-yl)benzene.

Workup

  1. temperaturebefore being warmed to RT
  2. additionwas added
  3. stirringthe reaction was stirred at RT for 1 h
  4. customThe mixture was quenched with 1 M HCl
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d22f2d8e9caa4da0a8a8dec636651141
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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