3-Nitrophenylboronic Acid → HCID 178442840, compound

HRID 343992Notes

Reaction equation

HRID 343992 reaction equation
[NH2:1][NH:2][C:3]([NH:5][NH2:6])=[S:4].[CH2:7]([C:22]1[CH:23]=[C:24]([CH:32]=[CH:33][CH:34]=1)[O:25][CH:26]([CH2:30][CH3:31])[C:27](O)=O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[N+](C1C=C(B(O)O)C=CC=1)([O-])=O>C1(C)C=CC=CC=1>[NH2:6][N:5]1[C:3]([SH:4])=[N:2][N:1]=[C:27]1[CH:26]([O:25][C:24]1[CH:32]=[CH:33][CH:34]=[C:22]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:23]=1)[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 85701Butanoic acid, 2-(3-pentadecylphenoxy)-HCID 2724189Thiocarbohydrazide

Product 1

HCID 178442840HCID 178442840, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2.65 g (25 mmol) of thiocarbohydrazide and 9.77 g (25 mmol) of 2-(3-pentadecylphenoxy)butanoic acid in 30 mL of toluene was added 0.42 g (2.5 mmol) of 3-nitrobenzene boronic acid was heated at reflux for 24 hr. The reaction was cooled and the reaction was allowed to settle. The supernatant liquid was decanted. To the residual solid was added 20 mL of acetonitrile. The mixture was stirred for 15 minutes. The solid was collected, rinsed with 5 mL of cold acetonitrile and dried in vacuo to afford 7.20 g (60.4%) of the desired product as a white solid. Analytical data are consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hr
  3. temperatureThe reaction was cooled
  4. customThe supernatant liquid was decanted
  5. additionTo the residual solid was added 20 mL of acetonitrile
  6. customThe solid was collected
  7. washrinsed with 5 mL of cold acetonitrile
  8. customdried in vacuo

Sources & evidence

ORD record
ord-fd15fe57b54949099606cbe393af5899
Source dataset
uspto-grants-1999_01
Patent number
US05864042

Reaction notes

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