HCID 20482499, compound → HCID 20482497, compound

HRID 648327Notes

Reaction equation

HRID 648327 reaction equation
CS(O[CH:6]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][CH:14]=1)(=O)=O.C([O-])(=[S:36])C.[K+]>CC(C)=O>[SH:36][CH:6]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 20482499HCID 20482499, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 20482497HCID 20482497, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7.6 g. ethyl 4-(6-methanesulfonyloxyhexadecylamino)benzoate and 5.5 g. of potassium thioacetate in 200 ml. of acetone is stirred under reflux for 3 hours and evaporated. The residue is positioned between methylene chloride and water and the organic layer is separated, dried and evaporated. Recrystallization of the residual solid form hexane affords the product as a light, tan solid. Hydrolysis of the product by the method of Example 10 affords 4-(6-mercaptohexadecylamino)benzoic acid.

Workup

  1. additionA mixture of 7.6 g
  2. temperatureunder reflux for 3 hours
  3. customevaporated
  4. customthe organic layer is separated
  5. customdried
  6. customevaporated
  7. customRecrystallization of the residual solid form hexane
  8. customaffords the product as a light, tan solid
  9. customHydrolysis of the product by the method of Example 10

Sources & evidence

ORD record
ord-ed36cef9cc944ab8a9a7faa93c25152a
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Reaction notes

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