Ethyl Thioglycolate → HCID 21469028, compound

HRID 1938329Notes

Reaction equation

HRID 1938329 reaction equation
[H-].[Na+].[SH:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]([C:22](=[O:32])[C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[CH2:14][CH2:13][C:12]=1[CH:33]=O>CN(C)C=O>[N+:29]([C:26]1[CH:27]=[CH:28][C:23]([C:22]([N:15]2[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:11]3[S:3][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:33][C:12]=3[CH2:13][CH2:14]2)=[O:32])=[CH:24][CH:25]=1)([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 21469040HCID 21469040, compound

Product 1

HCID 21469028HCID 21469028, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of 0.240 g (6.01 mmol) of sodium hydride (60% in oil) in 20 ml of N,N-dimethylformamide, chilled in an ice bath, is added 0.656 ml (6.01 mmol) of ethyl 2-mercaptoacetate. The mixture is stirred for 10 minutes and a slurry of 2.14 g (6.01 mmol) of 2,3-dihydro-5-chloro-1-(4-nitrobenzoyl)-1H-1-benzazepine-4-carboxaldehyde in 6 ml of N,N-dimethylformamide is added dropwise. The mixture is stirred at room temperature overnight and then concentrated under high vacuum. The residue is partitioned between chloroform and water and the organic layer separated. The aqueous layer is extracted (twice) with chloroform and the organic layer and extracts combined and dried (Na2SO4). The solvent is removed and the residue chromatographed on silica gel with dichloromethane as eluent (2 liter) and then with 4% ethyl acetate in dichloromethane as eluent. Fractions containing product are combined and the solvent removed under vacuum to give 2.1 g of ethyl 4,5-dihydro-6-(4-nitrobenzoyl)-6H-thieno[3,2-d][1]benzazepine-2-carboxylate as a yellow foam.

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. concentrationconcentrated under high vacuum
  3. customThe residue is partitioned between chloroform and water
  4. customthe organic layer separated
  5. extractionThe aqueous layer is extracted (twice) with chloroform
  6. dry with materialdried (Na2SO4)
  7. customThe solvent is removed
  8. customthe residue chromatographed on silica gel with dichloromethane as eluent (2 liter)
  9. additionFractions containing product
  10. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-24fcfc64e1b54cf5b1490bd1fc3cd676
Source dataset
uspto-grants-1997_12
Patent number
US05693635

Reaction notes

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