Ammonia → HCID 25208878, compound

HRID 1511816Notes

Reaction equation

HRID 1511816 reaction equation
[AlH3].[CH3:2][N:3]([CH2:5][CH2:6]O)[CH3:4].C(Cl)Cl.[NH3:11].[OH:12][S:13]([OH:16])(=O)=O.N.[C:18]1([CH3:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1.O.CO>[C:22]1([NH:11][S:13]([C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[CH2:20][C:21]([CH3:22])=[C:24]3[CH2:6][CH2:5][N:3]([CH3:4])[CH3:2])(=[O:16])=[O:12])[C:23]2[C:18](=[CH:24][CH:19]=[CH:18][CH:23]=2)[CH:19]=[CH:20][CH:21]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 1140TolueneHCID 22731429Ammonia dichloromethaneHCID 131729809HCID 131729809, compound

Product 1

HCID 25208878HCID 25208878, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

On a sufficient amount of anhydrous THF cooled to 0° C. 2 equivalents of a solution of AlH3-DMEA 0.5M in toluene were added. Then a solution, previously cooled to 0° C., of 1 equivalent of the previous amide in anhydrous THF was added. It was kept with stirring in an argon atmosphere at 0° C. for 30 minutes. The course of the reaction was followed by silica gel thin-layer chromatography (CH2Cl2/NH3 gas:MeOH 95:5). Water and H2SO4 10% were added to the reaction mixture and the temperature was allowed to rise slowly to 20° C. It was alkalinised with NH3 20% and extracted with AcOEt. The organic extracts, after being dried with anhydrous Na2SO4 and filtered, were evaporated to dryness. The residue obtained was purified by silica gel column chromatography (CH2Cl2/NH3 gas:MeOH, increasing polarity mixtures), providing N-(naphthalene-1-yl)-3-(2-dimethylaminoethyl)-2-methyl-1H-indene-5-sulfonamide.

Workup

  1. additionwas added
  2. customto rise slowly to 20° C
  3. extractionextracted with AcOEt
  4. dry with materialThe organic extracts, after being dried with anhydrous Na2SO4
  5. filtrationfiltered
  6. customwere evaporated to dryness
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography (CH2Cl2/NH3 gas:MeOH, increasing polarity mixtures)

Sources & evidence

ORD record
ord-7e11cd1ba90c4d5086e86f7a41f14c1a
Source dataset
uspto-grants-2012_07
Patent number
US08217041B2

Reaction notes

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