Dichloromethane → HCID 66747459, compound

HRID 2401786Notes

Reaction equation

HRID 2401786 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[S:10][C:11]=2[C:12]([O:14][CH2:15]C)=[O:13])=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1.C(Cl)Cl.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:17]3[CH:22]=[CH:21][N+:20]([O-:33])=[CH:19][CH:18]=3)[S:10][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 66747606HCID 66747606, compound

Product 1

HCID 66747459HCID 66747459, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazole-5-carboxylate (430 mg, 1.20 mmol) in DMF (6.0 mL) was added mCPBA (322 mg, 1.44 mmol) and the mixture was stirred at room temperature overnight. To the reaction was added DCM (30 mL) and saturated sodium bicarbonate (25 mL). The layers were separated and the aqueous layer extracted with DCM (20 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/DCM=50/50→100/0) to give 449 mg of the title compound as a white solid (100% yield). LC/MS (FA) ES+ 375. 1H NMR (300 MHz, CDCl3) δ: 8.23-8.20 (m, 2H), 7.84-7.81 (m, 2H), 7.33-7.23 (m, 4H), 4.51 (s, 2H), 4.38 (q, 2H, J=7.2 Hz), 1.39 (t, 3H, J=7.2 Hz).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with DCM (20 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/DCM=50/50→100/0)

Sources & evidence

ORD record
ord-5e3429588ff94e9a9ed9ef78c5ac0d77
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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