Ethanol → HCID 21469012, compound

HRID 1938330Notes

Reaction equation

HRID 1938330 reaction equation
[N+:1]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:14]3[S:21][C:22]([C:24]([O-:26])=[O:25])=[CH:23][C:13]=3[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.C(=O)(O)[O-].[Na+].[CH2:34](O)[CH3:35]>>[NH2:1][C:4]1[CH:28]=[CH:27][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:14]3[S:21][C:22]([C:24]([O:26][CH2:34][CH3:35])=[O:25])=[CH:23][C:13]=3[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 21469034HCID 21469034, compound

Product 1

HCID 21469012HCID 21469012, compound

Procedure

A mixture of ethyl (4,5-dihydro-6-(4-nitrobenzoyl)-6H-thieno[3,2-d][1]benzazepine-2-carboxylate (0.800 g) and 2.14 g of stannous chloride dihydrate in 36 ml of ethanol is refluxed for 1 hour, cooled to room temperature and diluted with ice water. The mixture is made basic with 10% sodium bicarbonate and stirred 3.8 hours. The mixture is extracted with chloroform and the extracts combined, treated with activated carbon and filtered through anhydrous magnesium sulfate. The filtrate is concentrated under vacuum to give 0.690 g of ethyl 4,5-dihydro-6-(4-aminobenzoyl)-6H-thieno[3,2-d][1]benzazepine-2-carboxylate as a tan foam: mass spectrum (CI) 393 (MH+).

Workup

  1. temperatureis refluxed for 1 hour
  2. extractionThe mixture is extracted with chloroform
  3. additiontreated with activated carbon
  4. filtrationfiltered through anhydrous magnesium sulfate
  5. concentrationThe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-c339b44642264029a1a384a7b8a6e465
Source dataset
uspto-grants-1997_12
Patent number
US05693635

Reaction notes

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