Ammonium Chloride → HCID 68644626, compound

HRID 1159742Notes

Reaction equation

HRID 1159742 reaction equation
[BH4-].[Na+].C([O:5][C:6]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]2[CH:19]=[C:18]([C:20](OCC)=[O:21])[CH:17]=[C:16]([C:25]3[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH:28]=[CH:27][N:26]=3)[N:15]=2)[CH:9]=1)=O)C.[Cl-].[NH4+].[BH4-]>C(O)C>[OH:5][CH2:6][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]2[CH:19]=[C:18]([CH2:20][OH:21])[CH:17]=[C:16]([C:25]3[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH:28]=[CH:27][N:26]=3)[N:15]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 59514875HCID 59514875, compound

Product 1

HCID 68644626HCID 68644626, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.2 g of sodium borohydride was added to a suspension of 4,4′-diethoxycarbonyl-4″-nonadecyl-2,2′:6′,2″-terpyridine (6.4 g, 10.0 mmol) in 200 mL of absolute ethanol. The mixture was refluxed for 3 h and cooled to room temperature, and then 200 mL of an ammonium chloride saturated water solution was added to decompose the excess borohydride. The ethanol was removed under vacuum and the precipitated solid was dissolved in a minimal amount of water. The resulting solution was extracted with ethyl acetate (5×200 mL) and dried over sodium sulfate, and the solvent was removed under vacuum. The desired solid was obtained in 79% yield and was used without further purification. Anal. C36H53N3O2: Calcd: C, 77.24; H, 9.54; N, 7.51. Found: C, 77.10; H, 9.47; N, 7.49. MS (ESIMS): m/z: 559.4.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. customThe ethanol was removed under vacuum
  3. dissolutionthe precipitated solid was dissolved in a minimal amount of water
  4. extractionThe resulting solution was extracted with ethyl acetate (5×200 mL)
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed under vacuum
  7. customThe desired solid was obtained in 79% yield
  8. customwas used without further purification

Sources & evidence

ORD record
ord-e47f975958ef46f5bce44537a7459e21
Source dataset
uspto-grants-2010_10
Patent number
US07812251B2

Reaction notes

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