Benzenesulfonic Acid → Benzamide

HRID 2199861Notes

Reaction equation

HRID 2199861 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.[NH2:22]CCN1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].C1(S(O)(=O)=O)C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([NH2:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7371Benzenesulfonic AcidHCID 10340Sodium CarbonateHCID 4082852-MorpholinoethylamineHCID 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 (61.30 mg, 0.200 mmol) prepared in Preparative Example 1 and 4-(2-aminoethyl)morpholine represented by Formula 99 (31.22 mg, 0.240 mmol) were prepared in 0.2 M solution, respectively, using a toluene solvent. After adding 1M sodium carbonate solution and 0.2 M acyl chloride solution to the above solutions, the mixture was vigorously shaken and agitated at room temperature overnight. After terminating the reaction, an aqueous layer was discarded using a tip while 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 using an elute solution (ethyl acetate/methanol/triethylamine, 20:2:1, v/v/v) was conducted to produce a benzamide compound represented by Formula 7 as a desired product (VVZ-006; 79.10 mg, 98.8% yield).

Workup

  1. stirringagitated at room temperature overnight
  2. customAfter terminating
  3. customthe reaction
  4. customwas moved to a cartridge tube
  5. customImpurities were removed
  6. customwhile separation and purification

Sources & evidence

ORD record
ord-61c4a97c6973454a9c0a95af05ddad22
Source dataset
uspto-grants-2016_06
Patent number
US09359346B2

Reaction notes

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