Dichloromethane → HCID 86654670, compound

HRID 2173038Notes

Reaction equation

HRID 2173038 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([I:9])[CH:6]=[C:5]1[CH:10]=[O:11].ClCCl.CCN(CC)CC.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>O>[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:1][CH2:2][CH2:3][N:4]2[CH:8]=[C:7]([I:9])[CH:6]=[C:5]2[CH:10]=[O:11])(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86654669HCID 86654669, compound

Product 1

HCID 86654670HCID 86654670, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled (0° C.) solution of 1-(2-hydroxyethyl)-4-iodo-1H-pyrrole-2-carbaldehyde (3.4 g, 12.83 mmol) and dichloromethane (25 mL) was added Et3N (7.15 mL, 51.3 mmol). After 5 minutes, 4-methylbenzene-1-sulfonyl chloride (2.81 g, 14.75 mmol) was added portion wise over a period of 15 minutes, and the reaction mixture was allowed to warm to room temperature. Following reaction at room temperature overnight, water was added and the resulting layers were separated. The aqueous layer was extracted with dichloromethane (50 mL). The organic layers were combined, washed with saturated aqueous NaHCO3 and brine, dried over sodium sulfate, and evaporated to give a brown residue. The residue was purified with petroleum ether to give the title compound as a brown solid, which was used without further purification (3.8 g, 71%). ESI-MS m/z [M+H]+ calc'd for C14H14INO4S, 420. found, 420.

Workup

  1. additionwas added
  2. customthe resulting layers were separated
  3. extractionThe aqueous layer was extracted with dichloromethane (50 mL)
  4. washwashed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto give a brown residue
  8. customThe residue was purified with petroleum ether

Sources & evidence

ORD record
ord-55aa7b248bd24c2893e6dde26e486dc3
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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