Hydrochloric Acid → HCID 69438481, compound

HRID 851871Notes

Reaction equation

HRID 851871 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([OH:8])=O)#[N:2].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1.[ClH:26].CN(C)CCCN=C=NCC.[ClH:38]>CN(C)C1C=CN=CC=1>[Cl:26][CH2:1][Cl:38].[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([NH:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([O:18][CH3:17])[CH:20]=1)=[O:8])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108243-MethoxyanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 230238503-Cyano-4-(2-methylpropoxy)benzoic acid

Product 1

HCID 69438481HCID 69438481, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

(20 mL) was added to a mixture of 3cyano-4-isobutyloxybenzoic acid (2.19 g, 10 mmol), m-anisidine (1.85 g, 15 mmol), 1-[3-(dimethylamino)propyl]3-ethylcarbodiimide hydrochloride (WSC•HCl, 3.83 g, 20 mmol), and 4-(dimethylamino)pyridine (244 mg, 2.0 mmol). The resulting mixture was then stirred for 21 hours at room temperature. To the mixture was added aqueous 1M hydrochloric acid (30 mL), and the resulting mixture was extracted with ethyl acetate (40 mL). The ethyl acetate portion was washed with aqueous saturated sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, and placed under reduced pressure to distill the solvent off. The residue was recrystallized from toluene, to give 2.87 g (yield 89%) of the desired compound in the form of a crystalline product.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (40 mL)
  2. washThe ethyl acetate portion was washed with aqueous saturated sodium hydrogen carbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationto distill the solvent off
  5. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-74fd9e26b8e841d38fa0f4539799a8d4
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

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