Triethylamine → 2,2-Dimethyl-2,3-dihydro-7-[N-methyl-N-(4-tert-butylphenylthiosulfenyl)carbamoyloxy] benzofuran

HRID 1112407Notes

Reaction equation

HRID 1112407 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([OH:11])[C:4]=2[O:3]1.[CH3:13][N:14]([S:18][S:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=1)[C:15](F)=[O:16].C(N(CC)CC)C>O1CCOCC1.O>[CH3:1][C:2]1([CH3:12])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][C:15](=[O:16])[N:14]([CH3:13])[S:18][S:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:27])([CH3:29])[CH3:28])=[CH:22][CH:21]=3)[C:4]=2[O:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 152782,3-Dihydro-2,2-dimethyl-7-benzofuranolHCID 23333006N-Methyl-N(4-t-Butylphenylthiosulfenyl) Carbamoyl Fluoride

Product 1

HCID 227640422,2-Dimethyl-2,3-dihydro-7-[N-methyl-N-(4-tert-butylphenylthiosulfenyl)carbamoyloxy] benzofuranYield 39.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4.0 g (0.024 m) of 2,2-dimethyl-2,3-dihydrobenzofuran-7-ol and 6.56 g (0.024 m) of N-methyl-N-(p-tert-butylphenylthiosulfenyl)carbamoyl fluoride in 25 ml of dioxane was added 2.45 g (0.024 m) of triethylamine. After 24 hours the reaction mixture was diluted with 200 ml of water and the product was extracted in ethylacetate. The organic extract was washed in turn with diluted sodium hydroxide and water, dried over MgSO4 and concentrated under reduced pressure. The product was crystallized from isopropyl ether to yield 4.0 g of a white solid, m.p. 150°-151° C.

Workup

  1. extractionthe product was extracted in ethylacetate
  2. extractionThe organic extract
  3. washwas washed in turn with diluted sodium hydroxide and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe product was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-8c6dde35167a4e79a633a4157c8375f4
Source dataset
uspto-grants-1978_10
Patent number
US04122204

Reaction notes

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