Hydrochloric Acid → HCID 59132675, compound

HRID 1993035Notes

Reaction equation

HRID 1993035 reaction equation
C(C1NC=CN=1)(C1[NH:4]C=CN=1)=O.[CH3:13][C:14]1[CH:35]=[CH:34][CH:33]=[CH:32][C:15]=1[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:29]#[C:30][CH3:31])[CH2:25][C:26](O)=[O:27])=[CH:20][CH:19]=1.[NH4+].[OH-].Cl>C1COCC1.O>[CH3:13][C:14]1[CH:35]=[CH:34][CH:33]=[CH:32][C:15]=1[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:29]#[C:30][CH3:31])[CH2:25][C:26]([NH2:4])=[O:27])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 16726098HCID 16726098, compound

Product 1

HCID 59132675HCID 59132675, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Carbonyl diimidazole (0.46 g, 2.84 mmol) was added to a solution of 3-[4-(2-Methyl-benzyloxy)-phenyl]-hex-4-ynoic acid (See Example 13) (0.73 g, 2.37 mmol) in anhydrous THF (10 mL). The mixture was stirred at room temperature for 2 hours. Concentrated NH4OH (10 mL) was then added to the mixture, and the reaction was stirred at room temperature overnight. The reaction mixture was poured into water (300 mL) and the solution was adjusted to pH=7 with conc. HCl. The aqueous layer was then extracted with 3×25 mL ethyl acetate. The combined organic layers were washed with water, followed by brine. The organic layer was then dried (Na2SO4) and concentrated under reduced pressure to yield 0.48 g (70%) of 3-[4-(2-Methyl-benzyloxy)-phenyl]-hex-4-ynoic acid amide (23.2) as a light yellow solid. LC/MSD m/e: 308.4 (M+H)

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. extractionThe aqueous layer was then extracted with 3×25 mL ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialThe organic layer was then dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c6fc3b717b984c419c2b698ce9ad21ba
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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