HCID 20482499, compound → HCID 20482497, compound

HRID 1106171Notes

Reaction equation

HRID 1106171 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 partitioned between methylene chloride and water and the organic layer is separated, dried and evaporated. Recrystallization of the residual solid from 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 residue is partitioned between methylene chloride and water
  5. customthe organic layer is separated
  6. customdried
  7. customevaporated
  8. customRecrystallization of the residual solid from hexane
  9. customaffords the product as a light, tan solid
  10. customHydrolysis of the product by the method of Example 10

Sources & evidence

ORD record
ord-a6cab2939f9f4e8997ff8116a8a61372
Source dataset
uspto-grants-1982_01
Patent number
US04311846

Reaction notes

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