m-Chloroperbenzoic acid → Methyl 6-(phenylsulfinyl)imidazo(1,2-a)pyridine-2-carbamate

HRID 1447605Notes

Reaction equation

HRID 1447605 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[CH:21]=1)=[O:4].ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:30])=[CH:10][N:9]2[CH:21]=1)=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12414300Methyl [6-(phenylsulfanyl)imidazo[1,2-a]pyridin-2-yl]carbamate

Product 1

HCID 191716Methyl 6-(phenylsulfinyl)imidazo(1,2-a)pyridine-2-carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alternatively, 0.599 g. (0.002 mole) of the product of Example 3 is combined with 0.406 g. (0.002 moles) of metachloroperbenzoic acid (85%) in 300 ml. of methylene chloride and stirred at room temperature overnight. The solution is washed with saturated aqueous sodium bicarbonate and evaporated to dryness affording 0.75 g. of crude product which is recrystallized from methylene chloride affording 2-(methoxycarbonylamino) 6-(phenylsulfinyl) imidazo [1,2-a] pyridine m.p. 247°-248° C.

Workup

  1. washThe solution is washed with saturated aqueous sodium bicarbonate
  2. customevaporated to dryness
  3. customaffording 0.75 g
  4. customof crude product which is recrystallized from methylene chloride

Sources & evidence

ORD record
ord-defae46c58974574a3ab55c3235e0339
Source dataset
uspto-grants-1979_12
Patent number
US04177274

Reaction notes

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