4-Nitrobenzoic Acid → Benzamide, 4-nitro-N-[3-(triethoxysilyl)propyl]-

HRID 1723304Notes

Reaction equation

HRID 1723304 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[NH2:17][CH2:18][CH2:19][CH2:20][Si:21]([O:28][CH2:29][CH3:30])([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24].C(N(CC)CC)C>C(OCC)C>[CH2:26]([O:25][Si:21]([O:28][CH2:29][CH3:30])([O:22][CH2:23][CH3:24])[CH2:20][CH2:19][CH2:18][NH:17][C:8](=[O:10])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=1)[CH3:27]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 8471TriethylamineHCID 13521(3-Aminopropyl)triethoxysilaneHCID 24386Thionyl Chloride

Product 1

HCID 109028Benzamide, 4-nitro-N-[3-(triethoxysilyl)propyl]-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

p-nitrobenzoic acid (10 g; 60 mmol) was added to 15 g thionylchloride. This mixture was heated during 2 h under reflux. Subsequently the thionylchloride was removed at reduced pressure. To the remainder γ-aminopropyltriethoxysilane (13,3 g; 60 mmol) was added, dissolved in 50 ml diethylether with 10 g triethylamine. After 2 h agitation at room temperature, the mixture was filtered. The filtrate was evaporated at reduced pressure. The remainder was washed in water, filtered, and dried at reduced pressure over KOH. Yield: 9,5 g (43%). Melting point 99° . . . 105° C.

Workup

  1. temperatureThis mixture was heated during 2 h
  2. temperatureunder reflux
  3. customSubsequently the thionylchloride was removed at reduced pressure
  4. filtrationthe mixture was filtered
  5. customThe filtrate was evaporated at reduced pressure
  6. washThe remainder was washed in water
  7. filtrationfiltered
  8. dry with materialdried at reduced pressure over KOH
  9. custom105° C.

Sources & evidence

ORD record
ord-a54380c831bd451aab609b4981e89518
Source dataset
uspto-grants-1989_08
Patent number
US04860573

Reaction notes

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