Potassium Carbonate → (5-Chlorothiophen-3-yl)methanamine hydrochloride

HRID 1685045Notes

Reaction equation

HRID 1685045 reaction equation
[Cl:1]N1C(=O)CCC1=O.[S:9]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10]1.C([O-])([O-])=O.[K+].[K+]>CCCCCC>[ClH:1].[Cl:1][C:13]1[S:9][CH:10]=[C:11]([CH2:14][NH2:15])[CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31398ChlorosuccinimideHCID 74231Thiophene-3-carbonitrile

Product 1

HCID 57415853(5-Chlorothiophen-3-yl)methanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of N-chlorosuccinimide (1.0 eq, 12.2 g) in hexane (100 mL) were added thiophene-3-carbonitrile (10 g, 91.6 mmol) and 70% HClO4 (1 mol %, 0.1 mL). The reaction mixture was stirred overnight at room temperature and subsequently K2CO3 was added. Removal of the solids and the volatiles afforded the crude product as a yellow oil. (This was a mixture of starting material: desired product: wrong isomer: dichlorinated 48%:26%:19%:6%.) Purification twice by column chromatography afforded 5-chlorothiophene-3-carbonitrile (1.71 g, 13%) as a yellow oil.

Workup

  1. customRemoval of the solids
  2. customthe volatiles afforded the crude product as a yellow oil
  3. additiona mixture of starting material

Sources & evidence

ORD record
ord-7565e5a9a84e4f958682b62a8fb6e441
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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