Diazomethane → HCID 53755453, compound

HRID 328387Notes

Reaction equation

HRID 328387 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][N:13]=[C:14]([C:23]([OH:25])=[O:24])[CH2:15][CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH2:9][N:8]=[C:7]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:6]=2[CH:32]=1.[N+](=[CH2:35])=[N-]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][N:13]=[C:14]([C:23]([O:25][CH3:35])=[O:24])[CH2:15][CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH2:9][N:8]=[C:7]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:6]=2[CH:32]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 53749252HCID 53749252, compound

Product 1

HCID 53755453HCID 53755453, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-chloro-2-[[1-carboxy-4-(diethylamino)butylidene]hydrazino]-5-phenyl-3H-1,4-benzodiazepine in CH2Cl2 (10 ml.) is treated with stirring under N2, with an ethereal solution of diazomethane (5 ml., 0.3 M). After 1/2 hour the solution is concentrated in vacuo giving 7-chloro-2-[[1-(methoxycarbonyl)-4-(diethylamino)-butylidene]hydrazino]-5-phenyl-3H-1,4-benzodiazepine as an oil, the nmr of which confirmed the structure. Nmr (CDCl3) δ 0.95 (t, 3, CH2CH3) 1.82 (m, 2, CH2CH2CH2); 2.50 (m, 6, CH2CH3 and CH2CH2N), 2.27 (m, z, CCH2CH2), 3.77 (s, 3, OCH3), 4.50 (broad s, z, 3--CH2), between 6.80 and 7.85 (m, 8, arom H's).

Workup

  1. concentrationAfter 1/2 hour the solution is concentrated in vacuo

Sources & evidence

ORD record
ord-a7e8d1b3ceb3499d9d66fdf215b5c650
Source dataset
uspto-grants-1977_04
Patent number
US04017492

Reaction notes

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