p-Toluenesulfonic acid → HCID 21162758, compound

HRID 894123Notes

Reaction equation

HRID 894123 reaction equation
[C:1]1([NH:7][C:8](=[O:12])[O:9][CH2:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16](S(O)(=O)=O)=[CH:15][CH:14]=1.[CH2:24]=C(C)C>C1(C)C=CC=CC=1>[CH3:24][CH:23]([C:4]1[CH:5]=[CH:6][C:1]([NH:7][C:8](=[O:12])[O:9][CH2:10][CH3:11])=[CH:2][CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7591Ethyl N-phenylcarbamateHCID 8255Isobutylene2×

Product 1

HCID 21162758HCID 21162758, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 165 parts of ethyl N-phenylcarbamate and 10 grams of p-toluenesulfonic acid is heated, in a stirred autoclave, to 100° C. whilst stirring, and 112 parts of isobutene are pumped in over two hours. After completion of the addition of isobutene, the mixture is stirred for a further two hours at 100° C. It is then diluted with 100 parts of toluene and extracted with aqueous sodium carbonate solution, and the end product is distilled under reduced pressure. 169 parts (72% of theory, based on carbamic acid ester II) of ethyl N-(4-tert.-butylphenyl)-carbamate, of boiling point 125°-127° C./0.2 mbar, are obtained. The conversion is 76 percent.

Workup

  1. customare pumped in over two hours
  2. stirringthe mixture is stirred for a further two hours at 100° C
  3. extractionextracted with aqueous sodium carbonate solution
  4. distillationthe end product is distilled under reduced pressure

Sources & evidence

ORD record
ord-0757a76cd1a641d594c7e96a564e6d5c
Source dataset
uspto-grants-1981_08
Patent number
US04282368

Reaction notes

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