Water → 2-[(2-bromophenyl)-hydrazono]-N-ethyl-2-cyanoacetamide

HRID 2375582Notes

Reaction equation

HRID 2375582 reaction equation
C(O[C:4](=[O:17])[C:5](=[N:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Br:16])[C:6]#[N:7])C.[CH2:18]([NH2:20])[CH3:19].O.C(N(CC)CC)C>CO>[Br:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][N:8]=[C:5]([C:6]#[N:7])[C:4]([NH:20][CH2:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6341EthylamineHCID 8471TriethylamineHCID 4084583[(2-Bromophenyl)-hydrazono]-cyanoacetic acid ethyl ester

Product 1

HCID 866130962-[(2-bromophenyl)-hydrazono]-N-ethyl-2-cyanoacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [(2-bromophenyl)-hydrazono]-cyanoacetic acid ethyl ester (1.0 g, 3.4 mmol) in methanol (14 mL) was added 70% ethyl amine in water (16 mL, 20.2 mmol) followed by triethyl amine (468 uL, 3.6 mmol). The reaction was stirred at room temperature overnight, concentrated and dried under high vacuum. The material was routinely used crude. Purification on silica gel using a gradient of 10to 50% ethyl acetate in hexanes afforded the title compound as a yellow solid. 1H NMR (300.132 MHz, CDCl3) δ 14.33 (s, 1H), 7.67 (dd, J=8.3, 1.4 Hz, 1H), 7.53 (dd, J=8.1, 1.3 Hz, 1H), 7.34 (tq, J=7.8, 0.6 Hz, 1H), 7.01 (td, J=7.7, 1.6 Hz, 1H), 3.45 (dq, J=5.9, 7.2 Hz, 2H), 1.26 (t, J=7.3 Hz, 3H). HPLC 4.66 min.

Workup

  1. concentrationconcentrated
  2. customdried under high vacuum
  3. customPurification on silica gel using a gradient of 10to 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4d9bfda2d6b74a5d9df9272052ffe89d
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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