p-Toluenesulfonic acid → 1-({2-[4-(3-Chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}methyl)pyrrolidin-2-one

HRID 1710803Notes

Reaction equation

HRID 1710803 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([CH2:18]O)=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.[NH:20]1[CH2:24][CH2:23][CH2:22][C:21]1=[O:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:13][C:14]([CH2:18][N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])=[C:15]([CH3:17])[N:16]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 120252-PyrrolidoneHCID 59457510{2-[4-(3-Chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}methanol

Product 1

HCID 594574631-({2-[4-(3-Chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}methyl)pyrrolidin-2-oneYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a flask fitted with a magnetic stirrer and a reflux condenser, {2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}methanol i109 (0.67 mmol, 1 eq, 0.2 g), pyrrolidinone (0.8 mmol, 1.2 eq, 0.069 g) and p-toluenesulfonic acid (0.067 mmol, 0.1 eq, 0.013 g) are dissolved in toluene (5 ml) and the mixture is brought to reflux overnight. After this time, the mixture is concentrated, taken up in ethyl acetate and washed with a saturated solution of sodium bicarbonate. The organic layer is dried over magnesium sulfate and concentrated to dryness to give 0.295 g of 1-({2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}methyl)pyrrolidin-2-one i110. This crude product is used in the next step without further purification.

Workup

  1. customIn a flask fitted with a magnetic stirrer and a reflux condenser
  2. temperatureto reflux overnight
  3. concentrationAfter this time, the mixture is concentrated
  4. washwashed with a saturated solution of sodium bicarbonate
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-919e2dae5549415296dc5a13fad8bcba
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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