Carbon Disulfide → HCID 23288038, compound

HRID 367308Notes

Reaction equation

HRID 367308 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16](=[S:18])=S.[C:19]([O:22][C:23]1[C:24]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:25][C:26]2[O:30][C:29]([CH2:32][NH2:33])([CH3:31])[CH2:28][C:27]=2[C:34]=1[C:35]([CH3:38])([CH3:37])[CH3:36])(=[O:21])[CH3:20]>O1CCCC1>[C:19]([O:22][C:23]1[C:24]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:25][C:26]2[O:30][C:29]([CH2:32][N:33]=[C:16]=[S:18])([CH3:31])[CH2:28][C:27]=2[C:34]=1[C:35]([CH3:38])([CH3:37])[CH3:36])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6348Carbon Disulfide2×HCID 10868DicyclohexylcarbodiimideHCID 154857245-Acetoxy-2-aminomethyl-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran

Product 1

HCID 23288038HCID 23288038, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To an ice-cooled suspension of 4.56 g of dicyclohexylcarbodiimide and 8 ml of carbon disulfide in 20 ml of tetrahydrofuran was added dropwise a solution of 6.18 g of 5-acetoxy-2-aminomethyl-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran synthesized in Example 70-5) in 20 ml of tetrahydrofuran. The mixture was stirred at 0° C. for 2 hours and then stirred at room temperature for 24 hours. After reaction, carbon disulfide and tetrahydrofuran were removed using an evaporator and the precipitated dicyclohexylthiourea was filtered off. Then, water was added to the filtrate and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography eluting with n-hexane containing 10% ethyl acetate to give 5.15 g of (5-acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl isothiocyanate (rotamer mixture) as a colorless oil (yield 74%).

Workup

  1. stirringstirred at room temperature for 24 hours
  2. customwere removed
  3. customan evaporator
  4. filtrationthe precipitated dicyclohexylthiourea was filtered off
  5. additionThen, water was added to the filtrate
  6. extractionthe solution was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe concentrate was purified by silica gel column chromatography
  11. washeluting with n-hexane containing 10% ethyl acetate

Sources & evidence

ORD record
ord-7f8f651034e146f58e701f4ac3ac566f
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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