Water → HCID 86744682, compound

HRID 359671Notes

Reaction equation

HRID 359671 reaction equation
[C:1]([N:9]([CH3:11])[OH:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:12]([C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([S:24](Cl)(=[O:26])=[O:25])=[CH:16][CH:15]=1)=[CH2:13].C(N(CC)CC)C.O>O1CCCC1>[CH:12]([C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([S:24]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:1]([N:9]([CH3:11])[OH:10])=[O:8])(=[O:26])=[O:25])=[CH:16][CH:15]=1)=[CH2:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 371715N-Hydroxy-N-methylbenzamideHCID 20063736HCID 20063736, compound

Product 1

HCID 86744682HCID 86744682, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.0 g of N-methylhydroxylamine hydrochloride was added to 100 ml of tetrahydrofuran. 19.8 g of pyridine was added to the mixture. A solution of 16.8 g of benzoyl chloride in 100 ml of tetrahydrofuran was dropwise added to the mixture under stirring at room temperature over 1 hr. The stirring was continued at room temperature for additional 8 hr. to conduct the reaction. 50 ml of dilute hydrochloric acid was added thereto and then tetrahydrofuran was removed under reduced pressure. After extraction with ethyl acetate, the extract was dehydrated over anhydrous magnesium sulfate. Ethyl acetate was removed under reduced pressure. The resultant crude product was purified according to column chromatography (packing: silica gel, developer: ethyl acetate/hexane) to obtain 8.5 g of N-benzoyl-N-methylhydroxylamine as an oil having a melting point of 20° C. or below. 130 ml of tetrahydrofuran was added to 7.6 g of N-benzoyl-N-methylhydroxylamine and 12.6 g of 4-vinyl-1-naphthalenesulfonyl chloride. A solution of 5.1 g of triethylamine in 20 ml of tetrahydrofuran was dropwise added thereto under stirring over 2 hr. while the mixture was cooled so that the temperature of the solution was below 25° C. After conducting the reaction at 15° to 25° C. for additional 2 hr., the reaction solution was poured into 700 ml of water and the precipitate thus formed was collected by filtration. After recrystallization from acetonitrile, 12.8 g of o-(4-vinyl-1-naphthalenesulfonyl)-N-benzoyl-N-methylhydroxylamine was obtained.

Workup

  1. temperaturewhile the mixture was cooled so that the temperature of the solution
  2. customwas below 25° C
  3. customthe reaction at 15° to 25° C. for additional 2 hr
  4. customthe precipitate thus formed
  5. filtrationwas collected by filtration
  6. customAfter recrystallization from acetonitrile

Sources & evidence

ORD record
ord-fbe4e42ea3d74995a82f2b03ee0d5420
Source dataset
uspto-grants-1991_03
Patent number
US05002853

Reaction notes

Loading…