Hydrochloric Acid → HCID 20228683, compound

HRID 1731364Notes

Reaction equation

HRID 1731364 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:11]1[CH:12]=[CH:13][C:14]2[S:18][C:17](=[O:19])[NH:16][C:15]=2[CH:20]=1.[H-].[Na+].[C:23]([O:26][CH2:27][CH2:28]Br)(=[O:25])[CH3:24].Cl>CN(C)C=O.O>[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:11]1[CH:12]=[CH:13][C:14]2[S:18][C:17](=[O:19])[N:16]([CH2:28][CH2:27][O:26][C:23](=[O:25])[CH3:24])[C:15]=2[CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 20228731HCID 20228731, compound

Product 1

HCID 20228683HCID 20228683, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(3-methylimidazo[1,2-a]pyridin-2-yl)-2-benzothiazolinone (2.8 g) and sodium hydride (50% suspension in oil, 0.96 g) in dry dimethylformamide (30 ml) was stirred at ambient temperature for 30 minutes. To the resultant mixture was added 2-bromoethyl acetate (3.34 g) at ambient temperature and stirred for 5 hours under the same condition. The reaction mixture was poured into water and adjusted to pH 7.0 with 10% hydrochloric acid. The neutrallized solution was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was subjected to column chromatography on silica gel eluting with a mixture of ethyl acetate and diisopropyl ether (8:2). The fractions containing the desired compound was combined and evaporated in vacuo. The crystalline residue was recrystallized from ethyl acetate to afford 5-(3-methylimidazo[1,2-a]pyridin-2-yl)-3-(2-acetoxyethyl)-2-benzothiazolinone (1.3 g). mp. 113°-115° C.

Workup

  1. stirringstirred for 5 hours under the same condition
  2. extractionThe neutrallized solution was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. additionthe residue was subjected to column chromatography on silica gel eluting with a mixture of ethyl acetate and diisopropyl ether (8:2)
  7. additionThe fractions containing the desired compound
  8. customevaporated in vacuo
  9. customThe crystalline residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-81f48a0d31f343e09088c917a3e82c84
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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