Butylamine → 2-[(2-bromophenyl)-hydrazono]-N-butyl-2-cyanoacetamide

HRID 2375585Notes

Reaction equation

HRID 2375585 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]([NH2:22])[CH2:19][CH2:20][CH3:21].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:22][CH2:18][CH2:19][CH2:20][CH3:21])=[O:17]

Participants

5

Reactant 3

HCID 8007Butylamine2×HCID 8471TriethylamineHCID 4084583[(2-Bromophenyl)-hydrazono]-cyanoacetic acid ethyl ester

Product 1

HCID 866130982-[(2-bromophenyl)-hydrazono]-N-butyl-2-cyanoacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a microwave vial charged with [(2-bromophenyl)-hydrazono]-cyanoacetic acid ethyl ester (387 mg, 1.31 mmol) was added methanol (3 mL) and n-butylamine (520 uL, 5.24 mmol). The reaction temperature rose approximately 30° C. and everything went into solution. After 25 minutes, additional n-butylamine (260 uL, mg, 2.6 mmol) and triethyl amine (182 uL, 1.3 mmol) were added. The reaction was stirred at room temperature overnight and then concentrated to afford the title compound which was used without further purification (420 mg, 99%). 1H NMR (300.132 MHz, CDCl3) δ 14.33 (s, 1H), 7.67 (dd, J=8.3, 1.5 Hz, 1H), 7.53 (dd, J=8.1, 1.3 Hz, 1H), 7.34 (td, J=7.8, 1.2 Hz, 1H), 7.01 (dt?ddd, J=6.1 Hz, J=8.0 Hz, J=1.5 Hz, 1H), 6.22 (bs, 1H), 3.40 (dt, J=5.9, 7.2 Hz, 2H), 1.65-1.35 (m, 4H), 0.96 (td, J=7.3, 1.9 Hz, 3H). MS APCI, m/z=323/325 (M+H). HPLC 2.94 min

Workup

  1. customrose approximately 30° C.
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a5607f29e72345bbb289e6ec7b00b0f9
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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