Isobutyric Acid → HCID 12221603, compound

HRID 2379319Notes

Reaction equation

HRID 2379319 reaction equation
[C:1]([OH:6])(=O)[CH:2]([CH3:4])[CH3:3].[N+:7]([C:10]1[CH:11]=[C:12]([S:16]([NH2:19])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH:2]([C:1]([NH:19][S:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=1)(=[O:18])=[O:17])=[O:6])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 6590Isobutyric AcidHCID 67138Benzenesulfonamide, 3-nitro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 12221603HCID 12221603, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of isobutyric acid (4.6 ml, 0.05 mol), 3-nitrophenyl sulphonamide (10.1 g, 0.05 mol) and 4-dimethylaminopyridine (6.1 g, 0.05 mol) in anhydrous dichloromethane (400 ml) under an atmosphere of nitrogen was added 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (9.6 g 0.05 mol). The mixture was stirred at ambient temperature for 20 h. The mixture was extracted with 1M NaOH and tile separated aqueous phase was acidified using 5M HCl. The solid which precipitated was collected by filtration, washed with water and dried under vacuum to afford the title compound (8.16 g, 60%) as a colourless powder. mp 136°-138° C. 1H NMR (360 MHz, D6 -DMSO) δ 0.95 (6H, d, J=6.8 Hz), 2.48 (1H, septet, J=6.8 Hz), 7.95 (1H, dd, J=8.1 and 8.1 Hz), 8.33 (1H, dd, J=8.0 and 1.4 Hz), 8.54 (1H, dd, J=8.0, 1.4 Hz), 8.60 (1H, dd, J=1.4 and 1.4 Hz), 12.38 (1H, brs).

Workup

  1. extractionThe mixture was extracted with 1M NaOH and tile
  2. customseparated aqueous phase
  3. customThe solid which precipitated
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-fce30d183fbd43a1b9c5b4fe4f94ab64
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

Loading…