Sodium Hydroxide → 2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine-9-methanol

HRID 262988Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:10]2[C:11]3[S:25][C:24]([Cl:26])=[CH:23][C:12]=3[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])=[N:14][CH2:15][C:9]2=[N:8][N:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[Cl:26][C:24]1[S:25][C:11]2[N:10]3[C:6]([CH2:4][OH:3])=[N:7][N:8]=[C:9]3[CH2:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:12]=2[CH:23]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 0.41 g of 2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine-9-carboxylic acid ethyl ester in 6.5 ml of absolute tetrahydrofuran is added dropwise with ice-cooling and stirring to a suspension of (0.078 g) of lithium aluminium hydride in 5 ml of absolute tetrahydrofuran. After stirring for 1 hour at 5° C., there is added dropwise 0.8 ml of 0.5-N sodium hydroxide. After filtration of the solid material, the solvent is evaporated and the residue taken up in methylene chloride. The solution is washed with 0.5-N sodium hydroxide, subsequently with water and, after drying, evaporated to dryness. By crystallization of the residue from ethyl acetate, there is obtained 2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine-9-methanol, melting point 219°-221° C.

Workup

temperaturecooling
filtrationAfter filtration of the solid material
customthe solvent is evaporated
washThe solution is washed with 0.5-N sodium hydroxide, subsequently with water
customafter drying
customevaporated to dryness
customBy crystallization of the residue from ethyl acetate

Sources & evidence

ORD record: ord-dd7103d1969d4caab51b0fba7ac39deb
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04155913

Reaction notes

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