7-chloro-2-methylmercapto-5-phenyl-3H-1,4-benzodiazepine → 1-[(p-methoxybenzyloxy)-methyl]-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine

HRID 2296061Notes

Reaction equation

HRID 2296061 reaction equation
CS[C:3]1[CH2:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:5]=2[N:4]=1.[CH3:21][O:22][C:23]1[CH:35]=[CH:34][C:26]([CH2:27][O:28][CH2:29][C:30]([NH:32][NH2:33])=O)=[CH:25][CH:24]=1>CN(C)P(=O)(N(C)C)N(C)C>[CH3:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][O:28][CH2:29][C:30]2[N:4]3[C:5]4[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:6]=4[C:7]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)=[N:8][CH2:9][C:3]3=[N:33][N:32]=2)=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 125708587-chloro-2-methylmercapto-5-phenyl-3H-1,4-benzodiazepineHCID 204730792-(p-Methoxybenzyloxy)acetic acid hydrazide

Product 1

HCID 204730871-[(p-methoxybenzyloxy)-methyl]-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 15,0 g 2-(methylthio)-5-phenyl-7-chloro-3H-1,4-benzodiazepine [cf. G. A. Archer et al., J. Org. Chem. 29, 231 (1964)] and 11,5 g 2-(p-methoxybenzyloxy)-acetic acid-hydrazide in 100 ml hexamethyl-phosphoric acid triamide is heated for 10 hours at 140°. The reaction mixture is worked up analogously to Example 1. The crude product is crystallised from ethyl acetate-petrol ether, whereby 1-[(p-methoxybenzyloxy)-methyl]-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine M.P. 157°-159° is obtained.

Workup

  1. customThe crude product is crystallised from ethyl acetate-petrol ether

Sources & evidence

ORD record
ord-994755303a3f46d0abde4c0d51282a08
Source dataset
uspto-grants-1984_01
Patent number
US04427590

Reaction notes

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