Hydrochloric Acid → HCID 14627815, compound

HRID 1030234Notes

Reaction equation

HRID 1030234 reaction equation
[C:1](=[S:19])([O:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:7]([OH:14])=[C:6]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:5]=1)[NH2:2].[CH2:20](OC(OCC)C[Cl:25])[CH3:21].O.Cl>C(O)(=O)C.C(OCC)C.C(OCC)(=O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[ClH:25].[C:15]([C:6]1[CH:5]=[C:4]([O:3][C:1]2[S:19][CH:20]=[CH:21][N:2]=2)[CH:9]=[C:8]([C:10]([CH3:11])([CH3:12])[CH3:13])[C:7]=1[OH:14])([CH3:18])([CH3:17])[CH3:16]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 121282-Chloro-1,1-diethoxyethaneHCID 14627811HCID 14627811, compound

Product 1

HCID 14627815HCID 14627815, compoundYield 65.8%

Reagents, catalysts & solvents 4

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

O-(3,5-Di-tert-butyl-4-hydroxyphenyl) thiocarbamate (1.00 g), 0.66 g of chloroacetaldehyde diethyl acetal and 0.03 g of p-toluenesulfonic acid monohydrate were dissolved in 6 ml of acetic acid, and the solution was heated at 95° C. for 1 hour. The reaction mixture was poured into water and extracted with chloroform. The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated. The crude product obtained was dissolved in 10 ml of diethyl ether, 1.1 ml of 4 N hydrogen chloride solution in ethyl acetate was added thereto, and the solid precipitate was collected by filtration and dried to give 0.80 g of the desired compound as a colorless solid.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialwith saturated aqueous sodium chloride solution, dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product obtained
  6. filtrationthe solid precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-ef6451412c7a40f9b818eaa255474c49
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

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