Iodine → 3-Iodo-2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine

HRID 1413430Notes

Reaction equation

HRID 1413430 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].II.[I:24]([O-])(=O)=O.[K+].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[I:24][C:21]1[N:9]2[CH:10]=[C:11]([S:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:13][C:8]2=[N:7][C:6]=1[NH:5][C:3]([O:2][CH3:1])=[O:4]

Participants

7

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 12414300Methyl [6-(phenylsulfanyl)imidazo[1,2-a]pyridin-2-yl]carbamateHCID 23665710Potassium Iodate

Product 1

HCID 542889483-Iodo-2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine (600 mg., 2 mmoles), iodine (420 mg., 3.2 mmoles) and potassium iodate (180 mg., 0.8 mmole) in 60% aqueous acetic acid (50 ml.) containing 2 ml. of concentrated sulfuric acid is stirred at room temperature for 48 hours. The solution is diluted with ice water and the pH adjusted to 8 with aqueous sodium bicarbonate. The reaction mixture is extracted with dichloromethane and the dried extracts are evaporated in vacuo to yield 3-iodo-2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine.

Workup

  1. additioncontaining 2 ml
  2. extractionThe reaction mixture is extracted with dichloromethane
  3. customthe dried extracts are evaporated in vacuo

Sources & evidence

ORD record
ord-72989007dde14c72a0a9172cbaf46e2e
Source dataset
uspto-grants-1981_02
Patent number
US04250174

Reaction notes

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