Ethanol → HCID 21467154, compound

HRID 1939190Notes

Reaction equation

HRID 1939190 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[C:4]([N:6]1[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[C:8]2[S:14][CH:15]=[CH:16][C:7]1=2)=[O:5].C(O)C.[BH4-].[Na+].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[C:4]([N:6]1[CH2:12][CH2:11][CH2:10][CH:9]([OH:13])[C:8]2[S:14][CH:15]=[CH:16][C:7]1=2)=[O:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 19699079HCID 19699079, compound

Product 1

HCID 21467154HCID 21467154, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.0 g of 4-(2-chloro-4-nitrobenzoyl)-4,5,6,7-tetrahydro-8H-thieno[3,2-b]azepin-8-one in 10 ml of tetrahydrofuran is added 1 ml of ethanol and the mixture cooled to 0° C. To the mixture is added 0.129 g of sodium borohydride in portions and the mixture is stirred at 0° C. for 1 hour. To the mixture is added slowly 4.2 ml of saturated ammonium chloride solution at 0° C. After stirring at room temperature for 10 minutes, the solvent is removed under vacuum and 80 ml of ethyl acetate added to the residue. The mixture is washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3 and brine. The organic layer is dried (Na2SO4) and filtered through a thin pad of hydrous magnesium silicate. The filtrate is concentrated under vacuum to give the product as a white glass.

Workup

  1. stirringAfter stirring at room temperature for 10 minutes
  2. customthe solvent is removed under vacuum and 80 ml of ethyl acetate
  3. additionadded to the residue
  4. washThe mixture is washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3 and brine
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. filtrationfiltered through a thin pad of hydrous magnesium silicate
  7. concentrationThe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-bae0fbc7f8a14b5a835e3aeb13d2b5a2
Source dataset
uspto-grants-1997_12
Patent number
US05696112

Reaction notes

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