1,2-Dichloroethane → N,N-diethyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzamide

HRID 1676931Notes

Reaction equation

HRID 1676931 reaction equation
[CH:1]1[CH:2]=[C:3]([CH2:6][NH:7][C:8]2[C:13]([C:14]([OH:16])=O)=[CH:12][C:11]([S:17]([NH2:20])(=[O:19])=[O:18])=[C:10]([Cl:21])[CH:9]=2)[O:4][CH:5]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH2:36]([NH:38][CH2:39][CH3:40])[CH3:37]>CN(C=O)C>[CH2:36]([N:38]([CH2:39][CH3:40])[C:14](=[O:16])[C:13]1[CH:12]=[C:11]([S:17]([NH2:20])(=[O:19])=[O:18])[C:10]([Cl:21])=[CH:9][C:8]=1[NH:7][CH2:6][C:3]1[O:4][CH:5]=[CH:1][CH:2]=1)[CH3:37]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 3440FurosemideHCID 8021DiethylamineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 46853521N,N-diethyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Example 7, furosemide can be reacted with EDC, HOBt and diethylamine in DMF to yield N,N-diethyl 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)-amino]benzamide.

Sources & evidence

ORD record
ord-64d47e73fdd743c4a291397a76a60f92
Source dataset
uspto-grants-2011_08
Patent number
US08008283B2

Reaction notes

Loading…