4-Toluenesulfonyl chloride → HCID 20320183, compound

HRID 866662Notes

Reaction equation

HRID 866662 reaction equation
Cl.[NH:2]1[C:6]([CH2:7][CH:8]=[O:9])=[CH:5][N:4]=[CH:3]1.C(N(CC)CC)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl>[S:23]([N:2]1[C:6]([CH2:7][CH:8]=[O:9])=[CH:5][N:4]=[CH:3]1)([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86735846HCID 86735846, compound

Product 1

HCID 20320183HCID 20320183, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.46 g (10 mM) of 2-(5-imidazolyl)-acetaldehyde HCl in 20 ml of dichloromethane is treated with 2.01 g (20 mM) of triethylamine and 1.9 g of p-toluenesulfonyl chloride at 25° C for about 16 hours after which the solution is washed with 3 N hydrochloric acid, water, sodium bicarbonate and water then dried and evaporated to afford 2-(1-tosylimidazol-5-yl)acetaldehyde upon recrystallization from ethyl acetate.

Workup

  1. washis washed with 3 N hydrochloric acid, water, sodium bicarbonate and water
  2. customthen dried
  3. customevaporated

Sources & evidence

ORD record
ord-dc92c47492064a84ba486f287d8e9d16
Source dataset
uspto-grants-1978_07
Patent number
US04100349

Reaction notes

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