Chloroform → HCID 53796021, compound

HRID 460744Notes

Reaction equation

HRID 460744 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH:12][CH2:13][CH2:14][CH2:15][C:16]1([CH3:23])[NH:20][C:19](=[O:21])[NH:18][C:17]1=[O:22].C(Cl)(Cl)Cl>N1C=CC=CC=1.O>[CH3:23][C:16]1([CH2:15][CH2:14][CH2:13][O:12][S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[NH:20][C:19](=[O:21])[NH:18][C:17]1=[O:22]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 213940595-(3-Hydroxypropyl)-5-methylimidazolidine-2,4-dione

Product 1

HCID 53796021HCID 53796021, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

P-toluenesulfonyl chloride (22.5 g., 0.118 mol) was added to a stirred solution of 5-(3-hydroxypropyl)-5-methyl-2,4-imidazolidine-dione (20.0 g, 0.116 mol) in pyridine (250 ml.) at 5° C. The mixture was stirred for one hour, refrigerated overnight and diluted with water (275 ml.) The resulting solution was extracted three times with chloroform (375, 190 and 190 ml.), the combined extracts were washed with 5 N aqueous sulfuric acid (4 × 125 ml.), water (2 × 150 ml.) and saturated aqueous sodium bicarbonate solution (2 × 125 ml). Concentration of the dried chloroform phase yielded 5-methyl-5- {3-[(4-methylphenyl)sulfonyloxy]-propyl}-2,4-imidazolinedione (22.2 g., 0.068 mol, 58%) upon addition of ether and petroleum ether, m.p. 126-127° C.

Workup

  1. extractionwas extracted three times with chloroform (375, 190 and 190 ml.)
  2. washthe combined extracts were washed with 5 N aqueous sulfuric acid (4 × 125 ml.), water (2 × 150 ml.) and saturated aqueous sodium bicarbonate solution (2 × 125 ml)

Sources & evidence

ORD record
ord-6975d5bcb744494598dbc69dcd393a92
Source dataset
uspto-grants-1977_12
Patent number
US04061542

Reaction notes

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