Phthalimide → 8-chloro-1-(2-phthalimidoethyl)-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine ethyl acetate

HRID 1731069Notes

Reaction equation

HRID 1731069 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15][CH2:16][OH:17])=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:24]=1.[C:25]1(=[O:35])[NH:29][C:28](=[O:30])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:28]([O:30][C:16](=[O:17])[CH3:15])[CH3:27].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15][CH2:16][N:29]4[C:25](=[O:35])[C:26]5=[CH:34][CH:33]=[CH:32][CH:31]=[C:27]5[C:28]4=[O:30])=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:6]=2[CH:24]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 125625088-chloro-1-(2-hydroxyethyl)-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 681397698-chloro-1-(2-phthalimidoethyl)-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine ethyl acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 8-chloro-6-phenyl-1-(2-hydroxyethyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine (0.677 g., 0.002 mole), phthalimide (0.324 g., 0.0022 mole), triphenylphosphine (0.576 g., 0.0022 mole) and dry tetrahydrofuran (20 ml.), under nitrogen, is treated with diethyl azodicarboxylate (0.383 g., 0.0022 mole) and stirred at ambient temperature (22°-25° C.) for 24 hours. The mixture is concentrated in vacuo and the residue chromatographed on silica gel (50 g.) with 3% methanol-97% chloroform. The product thus obtained is crystallized from ethyl acetate to give 8-chloro-1-(2-phthalimidoethyl)-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine ethyl acetate solvate of melting point 223.5°-226° C.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe residue chromatographed on silica gel (50 g.) with 3% methanol-97% chloroform
  3. customThe product thus obtained
  4. customis crystallized from ethyl acetate

Sources & evidence

ORD record
ord-1bbe1d1b945f4dda93f7dd66a8660759
Source dataset
uspto-grants-1976_11
Patent number
US03994941

Reaction notes

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