Hydrochloric Acid → HCID 69047344, compound

HRID 1985857Notes

Reaction equation

HRID 1985857 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[OH-].[Na+].Cl[S:22]([C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27]=[CH:28][CH:29]=[C:30]2[NH:35][C:36](=[O:38])[CH3:37])(=[O:24])=[O:23].Cl>O1CCOCC1.O.CO>[C:36]([NH:35][C:30]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:31]=1[CH:32]=[CH:33][CH:34]=[C:25]2[S:22]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)(=[O:24])=[O:23])(=[O:38])[CH3:37]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 655264-(Aminomethyl)Benzoic AcidHCID 50103065-Acetamidonaphthalene-1-sulfonyl chloride

Product 1

HCID 69047344HCID 69047344, compoundYield 85,397.203%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

4-(Aminomethyl)benzoic acid (726 mg, 4.8 mmol) and triethylamine (0.67 ml, 4.8 mmol) were dissolved in a mixed solution of 2N sodium hydroxide solution (2.4 ml, 4.8 mmol), dioxane (4.8 ml) and water (12 ml). A suspension of N-[5-(chlorosulfonyl)-1-naphthalenyl]acetamide (1.135 g, 4 mmol) in dioxane (4 ml) and methanol (12 ml) was added to the mixture under ice cooling and stirring, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into diluted hydrochloric acid, and the precipitated solid was washed with water and dried under reduced pressure to give the title compound as a light brown crystal (1,361 g, 85.4%).

Workup

  1. additionwas added to the mixture under ice cooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. washthe precipitated solid was washed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-33fd9daac7a54f9ab8a6626aaee32776
Source dataset
uspto-grants-2009_06
Patent number
US07547716B2

Reaction notes

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