m-Chloroperbenzoic acid → HCID 14709354, compound

HRID 641622Notes

Reaction equation

HRID 641622 reaction equation
[S:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[CH:6]=[N:5][C:4]=2[CH:3]=[CH:2]1.ClC1C=C(C=CC=1)C(OO)=[O:19]>C(Cl)(Cl)Cl>[S:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[CH:6]=[N+:5]([O-:19])[C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14452371HCID 14452371, compound

Product 1

HCID 14709354HCID 14709354, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Thieno[3,2-c]isoquinoline (13 g, 71 mmol) and 3-Chloroperoxybenzoic acid (57-86%, 21 g, 71 mmol) were combined in chloroform (300 mL) at 23° C. After 3 days the mixture was diluted with chloroform (750 mL), washed with 10% aqueous sodium hydroxide (2×500 mL) and brine (500 mL), dried (MgSO4), and concentrated in vacuo to give the crude product (13 g) as a yellow-brown solid. Recrystallization from hot ethanol (ca. 75 mL) provided the title compound (9.4 g, 66%, m.p. 190-95° C.) as dense brown needles.

Workup

  1. washwashed with 10% aqueous sodium hydroxide (2×500 mL) and brine (500 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give the crude product (13 g) as a yellow-brown solid
  5. customRecrystallization from hot ethanol (ca. 75 mL)

Sources & evidence

ORD record
ord-eed9717a0367494e91b613c0cbff0956
Source dataset
uspto-grants-2010_04
Patent number
US07696221B2

Reaction notes

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