Hydrochloric Acid → (5-Chlorothiophen-3-yl)methanamine hydrochloride

HRID 1685046Notes

Reaction equation

HRID 1685046 reaction equation
B.C1COCC1.[Cl:7][C:8]1[S:12][CH:11]=[C:10]([C:13]#[N:14])[CH:9]=1.Cl.O.CO>C1COCC1>[ClH:7].[Cl:7][C:8]1[S:12][CH:11]=[C:10]([CH2:13][NH2:14])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 22242641Methanol--water (1/1)HCID 574158585-Chlorothiophene-3-carbonitrile

Product 1

HCID 57415853(5-Chlorothiophen-3-yl)methanamine hydrochlorideYield 312.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a pre-cooled (ice-water bath) solution of BH3.THF (3.4 eq, 11.8 mL) was added a solution of 5-chlorothiophene-3-carbonitrile (0.5 g, 3.48 mmol) in THF (11.5 ml). The reaction mixture was stirred for 4 hours at room temperature and subsequently 6 N HCl (17 ml) was added slowly followed by H2O/MeOH (17/114 mL). The reaction mixture was stirred overnight. Removal of the volatiles afforded the title product (1.0 g) as an off-white solid.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customRemoval of the volatiles

Sources & evidence

ORD record
ord-e7da5c790395419ea648a7b77070da1d
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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