Pyrrole → HCID 19980540, compound

HRID 1461371Notes

Reaction equation

HRID 1461371 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.Cl[C:7]1[S:8][C:9]([N+:13]([O-:15])=[O:14])=[C:10]([Cl:12])[N:11]=1>CN1CCCC1=O>[Cl:12][C:10]1[N:11]=[C:7]([N:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)[S:8][C:9]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 8027PyrroleHCID 138518172,4-Dichloro-5-nitro-1,3-thiazole

Product 1

HCID 19980540HCID 19980540, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

6.7 g (0.1 mol) of pyrrole are added to a solution of 10.0 g (0.05 mol) of 2,4-dichloro-5-nitrothiazole in 100 ml of N-methyl-2-pyrrolidinone at room temperature. The mixture is then heated at 70° C. for 5 hours and subsequently cooled to room temperature and stirred into 1 l of ice-water. The precipitate formed is filtered off, washed with water and dried. 8.25 g (72.0% of theory) of 4-chloro-5-nitro-2-(1-pyrrolyl)-thiazole of melting point 138° C. to 139° C. (yellow needles from toluene) are obtained.

Workup

  1. temperaturesubsequently cooled to room temperature
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e69544b4948c40408e847fb220e1df5b
Source dataset
uspto-grants-1991_12
Patent number
US05075326

Reaction notes

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