Ammonia → 1-[(5-Acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]thiourea

HRID 367309Notes

Reaction equation

HRID 367309 reaction equation
[NH3:1].[C:2]([O:5][C:6]1[C:7]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:8][C:9]2[O:13][C:12]([CH2:15][N:16]=[C:17]=[S:18])([CH3:14])[CH2:11][C:10]=2[C:19]=1[C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:4])[CH3:3]>C(O)C>[C:2]([O:5][C:6]1[C:7]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:8][C:9]2[O:13][C:12]([CH2:15][NH:16][C:17]([NH2:1])=[S:18])([CH3:14])[CH2:11][C:10]=2[C:19]=1[C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 23288038HCID 23288038, compound

Product 1

HCID 232880401-[(5-Acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]thioureaYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 4.16 g of a 28% aqueous ammonia solution in 10 ml of ethanol was added dropwise a solution of 5.15 g of (5-acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl isothiocyanate in 20 ml of ethanol at room temperature. The mixture was stirred at room temperature for 2 hours, and then heated under reflux for further 1 hour. After cooling, ethanol was removed using an evaporator, and the mixture was combined with water and extracted with chloroform. 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 chloroform containing 10% methanol to give 5.3 g of 1-[(5-acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]thiourea (rotamer mixture) as a white solid (yield 99%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for further 1 hour
  3. temperatureAfter cooling
  4. customethanol was removed
  5. customan evaporator
  6. extractionextracted with chloroform
  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 chloroform containing 10% methanol

Sources & evidence

ORD record
ord-bd27f584722c44df996bff92a527185f
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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