Ammonium Chloride → HCID 67029513, compound

HRID 1465447Notes

Reaction equation

HRID 1465447 reaction equation
[Cl-].[C:2]([O:6][C:7]([NH:9][NH:10][C:11]([CH2:13][C:14]1[CH:39]=[CH:38][C:17]([CH2:18][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:16][CH:15]=1)=[O:12])=[O:8])([CH3:5])([CH3:4])[CH3:3].C([Li])CCC.[CH:45]([C:47]1[S:51][C:50]([NH:52][C:53](=[O:55])[CH3:54])=[CH:49][CH:48]=1)=O.[Cl-].[NH4+]>O1CCCC1>[C:53]([NH:52][C:50]1[S:51][C:47]([CH:45]=[CH:18][C:17]2[CH:16]=[CH:15][C:14]([CH2:13][C:11]([NH:10][NH:9][C:7]([O:6][C:2]([CH3:3])([CH3:4])[CH3:5])=[O:8])=[O:12])=[CH:39][CH:38]=2)=[CH:48][CH:49]=1)(=[O:55])[CH3:54]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 268899N-(5-Formyl-2-thienyl)acetamideHCID 86651838HCID 86651838, compoundHCID 178418339Butyllithium

Product 1

HCID 67029513HCID 67029513, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

{4-[2-(tert-Butoxycarbonyl)hydrazinocarbonylmethyl]benzyl}(triphenyl)phosphonium chloride (2.97 g, 5.29 mmol) was suspended in anhydrous tetrahydrofuran (8 ml), and cooled to −78° C. n-Butyllithium (1.6M-hexane solution, 3.3 ml, 5.3 mmol) was added dropwise, and the mixture was stirred at −78° C. for 15 mins and at 0° C. for 2 hrs. A solution of N-(5-formylthiophen-2-yl)acetamide (280 mg, 1.65 mmol) in anhydrous tetrahydrofuran (2 ml) was added dropwise, and the mixture was warmed to room temperature. After stirring at room temperature overnight, saturated aqueous ammonium chloride solution was added. The mixture was extracted with dichloromethane and the combined organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=97:3→80:20) to give tert-butyl 2-({4-[2-(5-acetylaminothiophen-2-yl)vinyl]phenyl}acetyl)hydrazinecarboxylate (192 mg, yield 28%, E/Z mixture) as a yellow solid.

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture was warmed to room temperature
  3. stirringAfter stirring at room temperature overnight
  4. extractionThe mixture was extracted with dichloromethane
  5. washthe combined organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=97:3→80:20)

Sources & evidence

ORD record
ord-774ebe64261c4fa0b72d0bc9e2d0b9f1
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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