Benzenesulfonic Acid → Benzamide

HRID 2199863Notes

Reaction equation

HRID 2199863 reaction equation
[CH2:1]([O:8]C1C(OC)=CC(C(Cl)=O)=CC=1OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:24]1CCC[C@H]1CN)C.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)(=O)C1C=CC=CC=1.C1(S(O)(=O)=O)C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([NH2:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 7371Benzenesulfonic AcidHCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 643457(S)-(-)-2-Aminomethyl-1-ethylpyrrolidineHCID 10267186Benzoyl chloride, 3,5-dimethoxy-4-(phenylmethoxy)-

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

First, 4-benzyloxy-3,5-dimethoxybenzoic acid chloride represented by Formula 85 and [(2S)-1-ethylpyrrolidin-2-yl]methanamine represented by Formula 103 were prepared in 0.2 M solution, respectively, using a toluene solvent. An amine solution (1.2 mL, 0.240 mmol) entered 10 mL vial and a sodium carbonate solution (0.4 mL, 0.200 mmol) was added thereto. Thereafter, a benzoic acid chloride solution (1.0 mL, 0.200 mmol) entered the vial, vigorously shaken and agitated at room temperature for 18 hours. After terminating the reaction, an organic layer was moved to a cartridge tube (6 mL, benzenesulfonic acid, 904030-WJ, UCT) using ethyl acetate. Impurities were removed using methanol (15 mL) while separation and purification were conducted using an elute solution (ethyl acetate/methanol/triethylamine, 20:2:1, v/v/v), resulting in a benzamide compound represented by Formula 13 as a desired product (VVZ-014; 66 mg, 83% yield).

Workup

  1. stirringagitated at room temperature for 18 hours
  2. customAfter terminating
  3. customthe reaction
  4. customan organic layer was moved to a cartridge tube
  5. customImpurities were removed
  6. customwhile separation and purification

Sources & evidence

ORD record
ord-0bc497babf5f4b909dfcbec05fe85def
Source dataset
uspto-grants-2016_06
Patent number
US09359346B2

Reaction notes

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