Hydrochloric Acid → HCID 9952783, compound

HRID 483453Notes

Reaction equation

HRID 483453 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])=[O:4].[CH3:14][C:15]([C:18]1[CH:23]=[C:22]([SH:24])[CH:21]=[C:20]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]=1[OH:29])([CH3:17])[CH3:16].C(N(CC)CC)C.Cl>C(#N)C>[CH3:28][C:25]([C:20]1[CH:21]=[C:22]([S:24][CH2:2][C:3]([NH:5][C:6]2[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:13])=[O:4])[CH:23]=[C:18]([C:15]([CH3:17])([CH3:16])[CH3:14])[C:19]=1[OH:29])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 9952783HCID 9952783, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared by dissolving 2-chloro-N-(2,6-dimethylphenyl)acetamide (1.8 g, 0.0091 mole) and 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (2.17 g, 0.0091 mole) in acetonitrile (20 ml) under argon. Triethylamine (1.25 ml) was added and the solution stirred at room temperature under argon for 12 hours. The solution was acidified with 10% hydrochloric acid with stirring, extracted with ethyl acetate (3×), the extracts combined, washed with water and dried over sodium sulfate. The solvent was removed on a rotary evaporator and the product purified by chromatography over silica and recrystallized from ethyl acetate/benzene. m.p. ca. 137.7° C.

Workup

  1. stirringwith stirring
  2. extractionextracted with ethyl acetate (3×)
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed on a rotary evaporator
  6. customthe product purified by chromatography over silica
  7. customrecrystallized from ethyl acetate/benzene

Sources & evidence

ORD record
ord-85c7143798b24829845aa96bd1cfbb87
Source dataset
uspto-grants-1993_07
Patent number
US05225444

Reaction notes

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