1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-bromothieno[2,3-c]furan-6(4H)-one
Reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[C:4]([CH2:10][OH:11])[CH:3]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]2[C:7](=[O:9])[O:11][CH2:10][C:4]=2[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In a 50 mL round bottom flask, 5-bromo-3-(hydroxymethyl)thiophene-2-carboxylic acid (140 mg, 0.59 mmol) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (113 mg, 0.59 mmol, 1.0 eq) were dissolved in DCM (5 mL) The solution was stirred at r.t. for 1 hr, concentrated and purified by flash column chromatography to give desired product. LC-MS (IE, m/z): 221.2 [M+1]+. 1H NMR (500 MHz, CDCl3, δ in ppm): 7.1 (1H, aromatic), 5.2 (2H, s).
Workup
- concentrationconcentrated
- custompurified by flash column chromatography
Sources & evidence
- ORD record
- ord-360bea5723c3499da47ccc3db9d821db
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056859B2
Reaction notes
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