N-bromobutanimide → 3-Bromo-2(methoxycarbonylamino)-6(phenylthio) imidazo [1,2-a] pyridine

HRID 1413429Notes

Reaction equation

HRID 1413429 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].[Br:22]N1C(=O)CCC1=O>ClCCl>[Br:22][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

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12414300Methyl [6-(phenylsulfanyl)imidazo[1,2-a]pyridin-2-yl]carbamate

Product 1

HCID 544631513-Bromo-2(methoxycarbonylamino)-6(phenylthio) imidazo [1,2-a] pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine (300 mg., 1 mmole) in 20 ml. of dichloromethane is treated with N-bromosuccinimide (220 mg., 1.24 mmole). The resultant solution is stirred at room temperature for 48 hours. The precipitate is collected by filtration, washed with dichloromethane and dried to yield 3-bromo-2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine m.p. 165°-168° C.

Workup

  1. filtrationThe precipitate is collected by filtration
  2. washwashed with dichloromethane
  3. customdried

Sources & evidence

ORD record
ord-9d42bcd3f1e14f78bf75188b0907eb7e
Source dataset
uspto-grants-1981_02
Patent number
US04250174

Reaction notes

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