Hydrochloric Acid → HCID 12112484, compound

HRID 1985855Notes

Reaction equation

HRID 1985855 reaction equation
[C:1]1([CH2:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:13]([NH:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[C:22]2[S:27](Cl)(=[O:29])=[O:28])(=[O:15])[CH3:14].C(N(CC)CC)C.Cl>O1CCCC1>[C:1]1([CH2:11][NH:12][S:27]([C:22]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:23]=2[CH:24]=[CH:25][CH:26]=[C:17]3[NH:16][C:13](=[O:15])[CH3:14])(=[O:29])=[O:28])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 83551-NaphthalenemethanamineHCID 8471TriethylamineHCID 50103065-Acetamidonaphthalene-1-sulfonyl chloride

Product 1

HCID 12112484HCID 12112484, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Naphthylmethylamine (174 mg, 1.1 mmol) was dissolved in tetrahydrofuran (10 ml), and 5-(acetylamino)-1-naphthalenesulfonyl chloride (284 mg, 1 mmol) was added under ice cooling and stirring. Then, triethylamine (0.17 mL, 1.2 mmol) was added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed successively with aqueous sodium hydrogen carbonate, water, and saturated brine, and after the layer was dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was crystallized by a mixed solvent of ethyl acetate/diisopropyl ether to give the title compound as a light brown crystal (325 mg, 80.4%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed successively with aqueous sodium hydrogen carbonate, water, and saturated brine
  4. dry with materialafter the layer was dried over anhydrous sodium sulfate
  5. customthe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas crystallized by a mixed solvent of ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-b6e0a3cbee5c4a56afae1ea808c3a996
Source dataset
uspto-grants-2009_06
Patent number
US07547716B2

Reaction notes

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