Water → 2'-Acetylamino-6'-(2-methanesulfonyloxypropyl)-3'-methoxy-4-nitrobenzophenone acetylhydrazone

HRID 2179899Notes

Reaction equation

HRID 2179899 reaction equation
[C:1]([NH:4][N:5]=[C:6]([C:16]1[C:21]([CH2:22][CH:23]([OH:25])[CH3:24])=[CH:20][CH:19]=[C:18]([O:26][CH3:27])[C:17]=1[NH:28][C:29](=[O:31])[CH3:30])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41].O>C(Cl)Cl>[C:1]([NH:4][N:5]=[C:6]([C:16]1[C:21]([CH2:22][CH:23]([O:25][S:40]([CH3:39])(=[O:42])=[O:41])[CH3:24])=[CH:20][CH:19]=[C:18]([O:26][CH3:27])[C:17]=1[NH:28][C:29](=[O:31])[CH3:30])[C:7]1[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 865844732'-Acetylamino-6'-(2-hydroxypropyl)-3'-methoxy-4-nitrobenzophenone acetylhydrazone

Product 1

HCID 865844742'-Acetylamino-6'-(2-methanesulfonyloxypropyl)-3'-methoxy-4-nitrobenzophenone acetylhydrazone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 23 (1.1 g) in 20 ml of CH2Cl2 was added 1.5 ml of triethyl amine, 0.60 ml of methanesulfonyl chloride at 0-10° C. After 30 min, no more starting material was detected on TLC. Water was added, extracted with CH2Cl2. The organic phase was washed with HCl (1N), brine, dried over Na2SO4. Removal of the solvent afforded product 24 (1.21 g).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic phase was washed with HCl (1N), brine
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-fef2f01eefd34a739a8096f360924edc
Source dataset
uspto-grants-2005_05
Patent number
US06887867B2

Reaction notes

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