Ethanethiol → HCID 15675929, compound

HRID 1460568Notes

Reaction equation

HRID 1460568 reaction equation
SCC.[Cl-].[Al+3].[Cl-].[Cl-].C(OC([NH:15][C:16]1[C:21]([CH3:22])=[C:20]([F:23])[CH:19]=[CH:18][C:17]=1[O:24]C)=O)(C)(C)C>ClCCl>[NH2:15][C:16]1[C:21]([CH3:22])=[C:20]([F:23])[CH:19]=[CH:18][C:17]=1[OH:24]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 15675928HCID 15675928, compound

Product 1

HCID 15675929HCID 15675929, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of mercaptoethane (56 ml) and dichloromethane (56 ml) was added aluminum chloride (22.4 g, 168 mmoles) under stirring at 0° C. To this was then added 2-(N-tert-butoxycarbonylamino)-4-fluoro-3-methylanisole (12.6 g, 56 mmoles) slowly at room temperature. Stirring continued for 11/2 hours. The reaction was quenched by adding ice and water and the solution acidified with 1N HCl. The organic substance was extracted with ethyl acetate (x3). The combined extracts were washed with NaHCO3 and with brine, dried over sodium sulfate and concentrated to give a solid. Recrystallization from chloroform gave 3.15 of pure title product; m.p. 118°-121° (dec).

Workup

  1. customslowly at room temperature
  2. stirringStirring
  3. custom2 hours
  4. customThe reaction was quenched
  5. additionby adding ice and water
  6. extractionThe organic substance was extracted with ethyl acetate (x3)
  7. washThe combined extracts were washed with NaHCO3 and with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customto give a solid
  11. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-5e97cb17140543b8bafeb3943d5b01bc
Source dataset
uspto-grants-1991_12
Patent number
US05071863

Reaction notes

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