Hydrochloric Acid → 4-(methoxycarbonyl)-2-methylthiophen-3-aminium chloride

HRID 2296359Notes

Reaction equation

HRID 2296359 reaction equation
[C:1]([CH:5]1[CH2:9][S:8][CH:7]([CH3:10])[C:6]1=[N:11]O)([O:3][CH3:4])=[O:2].[ClH:13]>CCOCC>[ClH:13].[NH2:11][C:6]1[C:5]([C:1]([O:3][CH3:4])=[O:2])=[CH:9][S:8][C:7]=1[CH3:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 73708224HCID 73708224, compound

Product 1

HCID 115067104-(methoxycarbonyl)-2-methylthiophen-3-aminium chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 41.1 g. (0.217 mole) of 4-carbomethoxy-3-keto-2-methyltetrahydrothiophene oxime in 600 ml. anhydrous ether, previously saturated with gaseous hydrogen chloride at 0°, was allowed to stir at 25° overnight. The separated solid was collected, washed well with ether, and dried to afford 33.2 g. Evaporation of the filtrate yielded after recrystallization of the residue an additional 4.2 g. to afford a total yield of pure 3-amino-4-carbomethoxy-2-methylthiophene hydrochloride of 37.4 g. (84%). The compound melts 191°-192°.

Workup

  1. customat 0°
  2. customThe separated solid was collected
  3. washwashed well with ether
  4. customdried
  5. customto afford 33.2 g
  6. customEvaporation of the filtrate
  7. customyielded
  8. customafter recrystallization of the residue an additional 4.2 g

Sources & evidence

ORD record
ord-b11d41955b4040d9bff8fd8f6ffb7011
Source dataset
uspto-grants-1984_01
Patent number
US04428963

Reaction notes

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