Ammonia → HCID 68818446, compound

HRID 735107Notes

Reaction equation

HRID 735107 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[CH2:6]([N:8]([CH2:22][CH3:23])[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][CH:13]=1)[CH3:7].N>S(=O)(=O)(O)O>[CH2:22]([N:8]([CH2:6][CH3:7])[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:16][C:17]=1[N+:1]([O-:4])=[O:2])[CH3:23]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24434Potassium NitrateHCID 408583N-[4-(2-DIETHYLAMINOETHOXY)PHENYL]ACETAMIDE

Product 1

HCID 68818446HCID 68818446, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

0.74 g (7.29 mmol) of potassium nitrate are added batchwise at −10° C. to a solution of 1.52 g (6.07 mmol) of N-[4-(2-diethylaminoethoxy)phenyl]acetamide in 25 mL of concentrated sulfuric acid and the mixture is stirred for 1 hour at −10° C. The reaction mixture is poured onto a mixture of ice and concentrated aqueous ammonia and the aqueous phase is exhaustively extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and evaporated down. Yield: 1.8 g (100% of theory); C14H21N3O4 (M=295.34); calc.: molecular ion peak (M+H)+: 296; found: molecular ion peak (M+H)+: 296; Rf value: 0.50 (Alox, dichloromethane/methanol (39:1)).

Workup

  1. extractionthe aqueous phase is exhaustively extracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. customevaporated down

Sources & evidence

ORD record
ord-519ab599dd144379a9b30b8495149c4e
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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