Ammonium Chloride → HCID 136045423, compound

HRID 2372861Notes

Reaction equation

HRID 2372861 reaction equation
Cl.[C:2]([NH2:8])(=[NH:7])[CH2:3][CH2:4][CH2:5][CH3:6].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([C:22]([CH3:24])=O)[C:17](OCC)=[O:18].[Cl-].[NH4+]>CN(C=O)C.[Cl-].[Na+].O.C[O-].[Na+]>[CH2:3]([C:2]1[NH:8][C:17](=[O:18])[C:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[Cl:9])=[C:22]([CH3:24])[N:7]=1)[CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 11615174Pentanimidamide HydrochlorideHCID 12273674HCID 12273674, compound

Product 1

HCID 136045423HCID 136045423, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 10942334Sodium MethoxideCatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 4.5 g valeramidine hydrochloride, 1.9 mg sodium methoxide, and 1.0 g ethyl 2-(2-chlorophenyl)acetoacetate in 20 mL DMF was heated to 150° C. for 20 hours. After cooling to room temperature, the reaction mixture was poured into a mixture of brine and saturated ammonium chloride solutions then was extracted three times with ether. The combined organic material was dried over MgSO4, stripped of solvent in vacuo, and MPLC'd in 40% ethyl acetate/hexane to give 212 mg of the title compound as a white solid, 37% yield. Rf 0.17 in 40% ethyl acetate/hexane; 1H NMR (300 MHz, CDCl3) δ7.55 (m, 1H), 7.38 (m, 2H), 7.26 (m, 1H), 4.64 (br s, 1H), 2.74 (3 line m, 2H), 2.11 (s, 3H), 1.79 (m, 2H), 1.42 (6 line m, 2H), 0.96 (t, 3H).

Workup

  1. extractionthen was extracted three times with ether
  2. dry with materialThe combined organic material was dried over MgSO4

Sources & evidence

ORD record
ord-62eedbaf83a344c0b1db57eb2145c1c3
Source dataset
uspto-grants-1992_03
Patent number
US05100897

Reaction notes

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