Trimethylamine → HCID 178468091, compound

HRID 654982Notes

Reaction equation

HRID 654982 reaction equation
[CH2:1]([NH:8][C:9]([CH:24]([CH3:33])[CH2:25][S:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[CH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C.[C:38](Cl)(=[O:40])[CH3:39]>C1C=CC=CC=1>[C:38]([C:10](=[C:9]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:24]([CH3:33])[CH2:25][S:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1)=[O:12])(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 6367Acetyl chlorideHCID 67833057HCID 67833057, compound

Product 1

HCID 178468091HCID 178468091, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

p-Nitrobenzyl 3-benzylamino-4-methyl-5-phenylthio-2-pentenoate (1.58 g; 3.51 mmole) was dissolved in tolune (5 ml), and trimethylamine (1.06 g; 10.5 mmole) was added thereto at 50° to 60° C. Acetyl chloride (630 mg; 8.0 mmole) was further added thereto all at once, and the resultant mixture was stirred for 10 minutes. Benzene (50 ml) was added to the reaction mixture, which was washed successively with a saturated sodium bicarbonate solution, water, dilute hydrochloric acid and an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give p-nitrobenzyl 2-acetyl-3-benzylamino-4-methyl-5-phenylthio-2-pentenoate.

Workup

  1. additionwas added
  2. customat 50° to 60° C
  3. washwas washed successively with a saturated sodium bicarbonate solution, water, dilute hydrochloric acid
  4. dry with materialan aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-234fd418203d4a98986d367b3ec009e0
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

Loading…