4-Toluenesulfonyl chloride → 2-(1-methyl-1H-pyrrol-2-yl)ethyl 4-methylbenzenesulfonate

HRID 1448348Notes

Reaction equation

HRID 1448348 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8][OH:9].[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:9][CH2:8][CH2:7][C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 117685722-(1-methyl-1H-pyrrol-2-yl)ethan-1-ol

Product 1

HCID 538724192-(1-methyl-1H-pyrrol-2-yl)ethyl 4-methylbenzenesulfonateYield 76.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred and cooled (±5° C.) mixture of 20.7 parts of 1-methyl-1H-pyrrole-2-ethanol and 200 parts of dry pyridine are added portionwise 35.9 parts of 4-methylbenzenesulfonyl chloride. Upon completion, stirring is continued for 6 hours at about 5° C. The reaction mixture is allowed to stand overnight at 0° C. and poured onto water. The product is extracted with benzene. The extract is washed successively with a 20% hydrochloric acid solution, water, a 10% sodium carbonate solution and with water, dried, filtered and evaporated, yielding 33.4 parts (76.8%) of 2-(1-methyl-1H-pyrrol-2-yl)ethyl 4-methylbenzenesulfonate as an oily residue.

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. waitto stand overnight at 0° C.
  4. additionpoured onto water
  5. extractionThe product is extracted with benzene
  6. washThe extract is washed successively with a 20% hydrochloric acid solution, water
  7. dry with materiala 10% sodium carbonate solution and with water, dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-0765e6343d5d455e86dce17a10d7e129
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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