m-Chloroperbenzoic acid → 7-Benzyloxy-2-ethylthiazolo[4,5-c]quinoline 5-oxide

HRID 913357Notes

Reaction equation

HRID 913357 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:21][C:20]([CH2:22][CH3:23])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:29]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:21][C:20]([CH2:22][CH3:23])=[N:19][C:14]=3[CH:15]=[N+:16]([O-:29])[C:17]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 673929657-Benzyloxy-2-ethylthiazolo[4,5-c]quinoline

Product 1

HCID 673930907-Benzyloxy-2-ethylthiazolo[4,5-c]quinoline 5-oxideYield 97.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 7-benzyloxy-2-ethylthiazolo[4,5-c]quinoline (15.0 g, 46.8 mmol) in chloroform (150 mL), 3-chloroperoxybezoic acid (m-CPBA. 50% w/w, 16.15 g, 46.8 mmol) was slowly added in small portions. The reaction was maintained at room temperature overnight. The reaction mixture was transferred to a separatory funnel and washed with 10% aqueous sodium carbonate (2×50 mL). The chloroform layer was concentrated to provide 15.4 g of 7-benzyloxy-2-ethylthiazolo[4,5-c]quinoline 5-oxide as a light tan solid. MS (ACPI) m/z=337 (M+H)+. This material was carried on without further purification to the next step.

Workup

  1. customThe reaction mixture was transferred to a separatory funnel
  2. washwashed with 10% aqueous sodium carbonate (2×50 mL)
  3. concentrationThe chloroform layer was concentrated

Sources & evidence

ORD record
ord-44242a4f06634ff3b11098be0f497e04
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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