Water → HCID 66616545, compound

HRID 1889638Notes

Reaction equation

HRID 1889638 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=O)[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.C(N=C=N[CH2:20][CH2:21][CH2:22][N:23](C)C)C.[CH:26]1C=CC2N(O)N=NC=2C=1.O.[CH2:37]([NH2:41])[CH:38]([CH3:40])[CH3:39]>CN(C=O)C.Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([NH:23][CH2:22][CH:21]([CH3:20])[CH3:26])=[O:9])[CH:5]=[C:4]([CH:3]=1)[C:11]([NH:41][CH2:37][CH:38]([CH3:40])[CH3:39])=[O:13]

Participants

9

Reactant 5

HCID 962WaterHCID 6558IsobutylamineHCID 750861,3-Benzenedicarboxylic acid, 5-chloro-HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 66616545HCID 66616545, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloroisophthalic acid (7.0 g, 34.9 mmol) in DMF (30 mL) were added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (16.73 g, 87.0 mmol) and HOBt.H2O (10.69 g, 69.8 mmol) at 0° C., followed by the addition of 10 mL of isobutylamine (8.67 mL, 87.0 mmol). The resulting mixture was stirred at rt for 3 h. The mixture was diluted with 1 N HCl solution and ethyl acetate. The organic layer was washed with brine, 1N NaOH solution, brine, dried over MgSO4 and concentrated to give a white solid (8.14 g, 72%). 1H NMR (CDCl3): δ 8.01 (d, J=1.6 Hz, 1H), 7.85 (d, T=1.6 Hz, 2H), 6.32 (m, 2H), 3.29 (dd, J=6.8, 6.4 Hz, 4H), 1.91 (m, 2H), 0.98 (d, J=6.8 Hz, 12H).

Workup

  1. washThe organic layer was washed with brine, 1N NaOH solution, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5c5284a123be4c338b0e034d38f53a04
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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