Triethylamine → HCID 14850389, compound

HRID 477526Notes

Reaction equation

HRID 477526 reaction equation
C(N(CC)CC)C.[C:8]1([C:14]([NH:27][C:28]2[S:29][CH:30]=[C:31](/[C:33](=[N:37]/[OH:38])/[C:34]([OH:36])=[O:35])[N:32]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:39]1[O:50][C:49]2[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][C:41]=2[O:40]1>ClCCl>[C:8]1([C:14]([NH:27][C:28]2[S:29][CH:30]=[C:31](/[C:33](=[N:37]/[O:38][C:44](=[O:45])[C:43]3[CH:47]=[CH:48][C:49]4[O:50][CH2:39][O:40][C:41]=4[CH:42]=3)/[C:34]([OH:36])=[O:35])[N:32]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 11732720HCID 11732720, compound

Product 1

HCID 14850389HCID 14850389, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (6.7 ml) was added with stirring to an ice-cooled suspension of 10 g of 2-(2-triphenylmethylamino-4-thiazolyl)-2-(Z-hydroxyimino)acetic acid in 140 ml of anhydrous dichloromethane. The suspension turned to a clear, faint yellow solution after ten minutes. A solution of 3,4-methylenedioxybenzoyl chloride (3.4 g) in 25 ml of dichloromethane was dropwise added and the mixture was stirred at room temperature for one hour. The insoluble crystals were removed by filtration and the filtrate was washed twice with 20 ml of 1N hydrochloric acid and 30 ml of saturated sodium chloride solution each, and dried over anhydrous sodium sulfate. The dried filtrate was concentrated under reduced pressure, and the viscous brown residue (14.2 g) was purified by silica gel column chromatography using chloroform/methanol (20-10:1) as eluent, affording 2.3 g of the objective compound as light brown crystals.

Workup

  1. temperaturecooled
  2. customafter ten minutes
  3. customThe insoluble crystals were removed by filtration
  4. washthe filtrate was washed twice with 20 ml of 1N hydrochloric acid and 30 ml of saturated sodium chloride solution each, and
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe dried filtrate was concentrated under reduced pressure
  7. customthe viscous brown residue (14.2 g) was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-41b323c044014f24820b98f8be9fa4ef
Source dataset
uspto-grants-1989_12
Patent number
US04888332

Reaction notes

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