1,2-Dichloroethane → 1-Hydroxybenzotriazole

HRID 989639Notes

Reaction equation

HRID 989639 reaction equation
[OH2:1].C(Cl)CCl.C(N1C2C=CC(C(O)=O)=CC=2C[N:12]([CH3:23])C(=O)C1CC(OC)=O)(=O)C.N[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([NH2:37])N=1.C[N:39](C=O)C>>[CH:35]1[CH:36]=[CH:31][C:23]2[N:12]([OH:1])[N:39]=[N:37][C:33]=2[CH:34]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 6228Dimethylformamide2×HCID 88612,6-DiaminopyridineHCID 86758535HCID 86758535, compound

Product 1

HCID 757711-HydroxybenzotriazoleYield 70%

Procedure

H2O (0.54 g, 3.6 mmol) and EDC (0.686 g, 3.6 mmol) were added to a solution of methyl (±)-1-acetyl-7-carboxy-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (1.0 g, 3 mmol) in dry DMF (15 mL). After 1 h the reaction solution was added dropwise to a solution of 2,6-diaminopyridine (0.326 g, 3.0 mmol) in dry DMF (20 mL). The reaction solution was stirred for 18 h, then was concentrated. Chromatography (silica gel, 9:1 CH2Cl2/MeOH) gave the title compound (0.9 g, 70%): 1H NMR (400 MHz, DMSO-d6) δ1.80 (s, 3H), 2.3-2.7 (m, 2H), 3.0-3.1 (s, 3H), 3.5-3.6 (s, 3H), 4.1-4.2 (d, 1H), 4.7-4.8 (d, 1H), 5.7-5.9 (m, 3H), 6.2-6.3 (d, 1H), 7.3-7.5 (m, 3H), 8.0-8.1 (d, 1H), 8.2-8.3 (s, 1H); MS (ES) m/e 426.0 (M+H)+.

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-0978074fc5bb49e6b4550c746a808471
Source dataset
uspto-grants-2002_10
Patent number
US06458784B1

Reaction notes

Loading…