Chlorine → 4-(methoxycarbonyl)-2-methylthiophen-3-aminium chloride

HRID 2076339Notes

Reaction equation

HRID 2076339 reaction equation
[NH2:1][C:2]1[CH:6]([CH3:7])[S:5][CH2:4][C:3]=1[C:8]([O:10][CH3:11])=[O:9].[Cl:12]Cl>C(Cl)Cl>[ClH:12].[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][S:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 16744634HCID 16744634, compound

Product 1

HCID 115067104-(methoxycarbonyl)-2-methylthiophen-3-aminium chlorideYield 115.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.6 g of methyl 4-amino-5-methyl-2,5-dihydrothiophene-3-carboxylate (2) (30 mmol, content: 93%) were dissolved in 30 ml of CH2Cl2. 2.3 g of chlorine (33 mmol) were introduced into this solution at room temperature over a period of 60 min. The reaction mixture was subsequently stirred for another 12 h and then, for workup, concentrated under reduced pressure. 7.2 g of methyl 4-amino-5-methylthiophene-3-carboxylate hydrochloride (5) were obtained (59% of theory, content: 42%, determined as the free amine).

Workup

  1. concentrationfor workup, concentrated under reduced pressure

Sources & evidence

ORD record
ord-7740f6b5090642ad9a43db50d406684d
Source dataset
uspto-grants-2011_04
Patent number
US07923571B2

Reaction notes

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