Hydrochloric Acid → HCID 9952783, compound

HRID 1460641Notes

Reaction equation

HRID 1460641 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 (3X), 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 (3X)
  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, m.p. ca. 137.7° C.

Sources & evidence

ORD record
ord-f04821df7ba74b258180045595f1f022
Source dataset
uspto-grants-1991_12
Patent number
US05071876

Reaction notes

Loading…