Acetic Acid → HCID 13922107, compound

HRID 1030228Notes

Reaction equation

HRID 1030228 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:16][C:17]([NH2:19])=[S:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].O.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24](S(O)(=O)=O)=[CH:23][CH:22]=1.[C:32](O)(=O)C>>[C:1]([C:5]1[CH:6]=[C:7]([NH:16][C:17]2[S:18][C:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:21][CH3:31])=[CH:32][N:19]=2)[CH:8]=[C:9]([C:12]([CH3:13])([CH3:15])[CH3:14])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 13281940HCID 13281940, compound

Product 1

HCID 13922107HCID 13922107, compound

Conditions

Temperature
90 °C

Procedure

3,5-Di-tert-butyl-4-hydroxyphenylthiourea (2.00 g), 1.81 g of α-bromooctylaldehyde dimethyl acetal and 0.06 g of p-toluenesulfonic acid monohydrate were dissolved in 12 ml of acetic acid, and the solution was heated at 90° C. for 1 hour. The reaction mixture was concentrated, saturated aqueous sodium bicarbonate solution was added, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated. Purification of the crude product by silica gel column chromatography (diethyl ether-hexane=1:3) gave 1.56 g of the desired compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionsaturated aqueous sodium bicarbonate solution was added
  3. extractionthe resultant mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification of the crude product by silica gel column chromatography (diethyl ether-hexane=1:3)

Sources & evidence

ORD record
ord-43d06b0e021a4a1d84ebee2cb2256342
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

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