Ethylene Glycol → HCID 20383037, compound

HRID 1447811Notes

Reaction equation

HRID 1447811 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]3[C:13]([CH2:16][O:17]S(C)(=O)=O)=[N:14][N:15]=[C:11]3[CH2:10][N:9]=[C:8]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:7]=2[CH:28]=1.[CH2:29](O)[CH2:30][OH:31]>>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]3[C:13]([CH2:16][O:17][CH2:29][CH2:30][OH:31])=[N:14][N:15]=[C:11]3[CH2:10][N:9]=[C:8]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:7]=2[CH:28]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 5360545SodiumHCID 20406677HCID 20406677, compound

Product 1

HCID 20383037HCID 20383037, compound

Procedure

A solution, prepared at 70°, of 2.83 g of sodium in 200 ml of ethylene glycol is treated with 24.8 g of 8-chloro-1-methylsulphonyloxymethyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine (c.f. German Offenlegungsschrift 2,201,210, Example 1) and the mixture is stirred for 6 hours at 70°. The reaction mixture is partitioned between ethyl acetate and water. The organic phase is separated off, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and evaporated. Crystallisation from ethyl acetate gives 8-chloro-1-(2-hydroxyethoxy-methyl)-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine, melting point 162°-164°.

Workup

  1. customThe reaction mixture is partitioned between ethyl acetate and water
  2. customThe organic phase is separated off
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-6d730b6b28d14afa8adefd408a0d659e
Source dataset
uspto-grants-1979_12
Patent number
US04178378

Reaction notes

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