2-Mercaptoethanol → HCID 19833014, compound

HRID 2051159Notes

Reaction equation

HRID 2051159 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[C:10]([C:14]([F:17])([F:16])[F:15])=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:18]=[N:19][C:20]([CH:21]=[O:22])=[C:4]2[CH2:3]1.[B].[SH:24][CH2:25][CH2:26]O>ClCCl>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[C:10]([C:14]([F:15])([F:17])[F:16])=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:18]=[N:19][C:20]([CH:21]3[S:24][CH2:25][CH2:26][O:22]3)=[C:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 5462311Boron2×HCID 19833021HCID 19833021, compound

Product 1

HCID 19833014HCID 19833014, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 400 mg (1.29 mmol) of 5,6-dihydro-5-methyl-6-oxo-7-trifluoromethyl-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde in 12 ml of dichloromethane with 0.04 ml of boron trifluoroethate, there was added a solution of 0.18 ml (1.29 mmole) of 2-mercaptoethanol in 40 ml of dichloromethane dropwise over 5 hours. After 18 hours further 0.02 ml of boron trifluoroetherate was added and the reaction mixture was stirred for 24 hours at ambient temperature. The reaction mixture was extracted with aqueous sodium bicarbonate, water, dried over MgSO4 and concentrated in vacuo to obtain a 47% yield of 5,6-dihydro-5-methyl-3-(1,3-oxathiolan-2-yl)-7-trifluoromethyl-imidazo[1,5-a][1,4]benzodiazepine-6(4H)-one after chromatography over silica gel.

Workup

  1. extractionThe reaction mixture was extracted with aqueous sodium bicarbonate, water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19a24814d023495a9f3736b8f83c0dbb
Source dataset
uspto-grants-1991_05
Patent number
US05017574

Reaction notes

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