Chloroacetic Acid → 8-chloro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo-[4,3-a][1,4]benzodiazepine

HRID 1413360Notes

Reaction equation

HRID 1413360 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][NH2:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:6]=2[CH:21]=1.[Cl:22][CH2:23][C:24](Cl)=O.ClCC(O)=O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:24]([CH2:23][Cl:22])=[N:13][N:12]=[C:10]3[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:6]=2[CH:21]=1

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 6577Chloroacetyl chlorideHCID 123908757-Chloro-5-(2-chlorophenyl)-2-hydrazinyl-3H-1,4-benzodiazepine

Product 1

HCID 126123488-chloro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo-[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the manner given in Preparation 5, 7-chloro-5-(o-chlorophenyl)-3H-1,4-benzodiazepin-2-yl hydrazine (31.9 g., 0.1 mole) was reacted with chloroacetyl chloride (11.3 g. 0.1 mole) the resulting chloroacetic acid, 2-(7-chloro-5-(o-chlorophenyl)-3H-1,4-benzodiazepin-2-yl)hydrozide was cyclized in hot acetic acid to give 8-chloro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine. The analytical sample had a melting point of 195°-198° C. with decomposition.

Sources & evidence

ORD record
ord-78c8d87836054df19db2e781bab536fd
Source dataset
uspto-grants-1981_02
Patent number
US04250094

Reaction notes

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