Hydrochloric Acid → 1H-Pyrrole, 2-(methylthio)-3-nitro-

HRID 1979731Notes

Reaction equation

HRID 1979731 reaction equation
Cl.[N+:2]([CH:5]=[C:6]([S:16][CH3:17])[NH:7][CH2:8][CH:9](OCC)OCC)([O-:4])=[O:3].C(=O)([O-])[O-].[K+].[K+]>CCOCC>[CH3:17][S:16][C:6]1[NH:7][CH:8]=[CH:9][C:5]=1[N+:2]([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 71398340N-(2,2-Diethoxyethyl)-1-(methylsulfanyl)-2-nitroethen-1-amine

Product 1

HCID 1516651H-Pyrrole, 2-(methylthio)-3-nitro-Yield 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dry hydrogen chloride was passed through a stirred solution of 1-nitro-2-methylthio-2-(2,2-diethoxyethylamino)-ethylene (9.7 g, 0.04 mol) in dry ether (250 ml) at 5°-10° for 3 hours. The resulting mixture was basified by pouring it into potassium carbonate solution (300 ml). The mixture was filtered to give a yellow solid, and the aqueous phase of the filtrate was separated and extracted with ether (2×150 ml). The combined ether solutions were evaporated to a residue. This residue and the solid filtered off earlier were recrystallised from acetone-chloroform to give 2-methylthio-3-nitropyrrole (3.4 g, 54%) m.p. 212°-213°.

Workup

  1. filtrationThe mixture was filtered
  2. customto give a yellow solid
  3. customthe aqueous phase of the filtrate was separated
  4. extractionextracted with ether (2×150 ml)
  5. customThe combined ether solutions were evaporated to a residue
  6. filtrationThis residue and the solid filtered off
  7. customearlier were recrystallised from acetone-chloroform

Sources & evidence

ORD record
ord-fd59d10b7b164f4991be755e7f80096b
Source dataset
uspto-grants-1984_11
Patent number
US04482563

Reaction notes

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