1,1'-Carbonyldiimidazole → 3-phthalimidovaleric acid, 2-(7-nitro-5-(o-chlorophenyl)-3H-1,4-benzodiazepin-2-yl)hydrazide

HRID 597085Notes

Reaction equation

HRID 597085 reaction equation
[C:1]1(=[O:18])[N:5]([CH:6]([CH2:11][CH3:12])[CH2:7][C:8]([OH:10])=O)[C:4](=[O:13])[C:3]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:2]12.C(N1C=CN=C1)(N1C=CN=C1)=O.[N+:31]([C:34]1[CH:35]=[CH:36][C:37]2[N:43]=[C:42]([NH:44][NH2:45])[CH2:41][N:40]=[C:39]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[Cl:52])[C:38]=2[CH:53]=1)([O-:33])=[O:32]>O1CCCC1>[N+:31]([C:34]1[CH:35]=[CH:36][C:37]2[N:43]=[C:42]([NH:44][NH:45][C:8](=[O:10])[CH2:7][CH:6]([N:5]3[C:1](=[O:18])[C:2]4=[CH:17][CH:16]=[CH:15][CH:14]=[C:3]4[C:4]3=[O:13])[CH2:11][CH3:12])[CH2:41][N:40]=[C:39]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[Cl:52])[C:38]=2[CH:53]=1)([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 202918567-nitro-2-hydrazino-5-(o-chlorophenyl)-3H-1,4-benzodiazepineHCID 214489983-Phthalimidovaleric acid

Product 1

HCID 867345673-phthalimidovaleric acid, 2-(7-nitro-5-(o-chlorophenyl)-3H-1,4-benzodiazepin-2-yl)hydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the manner given in Example 20, 3-phthalimidovaleric acid and carbonyldiimidazol are reacted in tetrahydrofuran. To this mixture is added 7-nitro-2-hydrazino-5-(o-chlorophenyl)-3H-1,4-benzodiazepine to give 3-phthalimidovaleric acid, 2-(7-nitro-5-(o-chlorophenyl)-3H-1,4-benzodiazepin-2-yl)hydrazide which is warmed with acetic acid to give N-[2-[8-nitro-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepin-1-yl]butyl]phthalimide.

Sources & evidence

ORD record
ord-512f0bd8a27741a591c49e2461767217
Source dataset
uspto-grants-1977_03
Patent number
US04012413

Reaction notes

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