Dimethylformamide → 3-[3-Benzyl-5-(1,3-dimethyl-1,3-dihydrobenzoimidazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-4-(ethylamino)benzonitrile

HRID 1241960Notes

Reaction equation

HRID 1241960 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][S:10][C:9]1=[N:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[NH:23][CH2:24][CH3:25])[C:18]#[N:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]1[CH2:36][CH2:35][N:34]2[C:29](=[N:30][CH2:31]C[CH2:33]2)[CH2:28][CH2:27]1.[CH3:37]N(C=O)C>>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:29]2[N:34]([CH3:33])[C:35]3[CH:37]=[CH:28][CH:27]=[CH:26][C:36]=3[N:30]2[CH3:31])[S:10][C:9]1=[N:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[NH:23][CH2:24][CH3:25])[C:18]#[N:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219373763-(3-Benzyl-4-oxothiazolidin-2-ylideneamino)-4-ethylaminobenzonitrile

Product 1

HCID 219375643-[3-Benzyl-5-(1,3-dimethyl-1,3-dihydrobenzoimidazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-4-(ethylamino)benzonitrile

Conditions

Temperature
100 °C

Procedure

To a solution of the above salt (66 mg, 0.2 mmol) and 3-(3-benzyl-4-oxothiazolidin-2-ylideneamino)-4-(ethylamino)benzonitrile (70 mg, 0.2 mmol) in DMF was added DBU (62 mL, 2 equiv) and the solution was heated to 100° C. for 48 h. Evaporation of solvent under high vacuum gave a crude, which was purified by chromatography on silica gel eluting with EtOAc-hexane (1:1) to give the title compound (3.6 mg). 1H-NMR indicated one isomer. 1H-NMR (CDCl3): δ 7.46 (2H, m), 7.22–7.36 (8H, m), 6.46 (1H, d), 5.17 (2H, s), 4.44 (1H, t), 3.79 (3H, s), 3.01 (2H, m), 0.88 (3H, t); MS (ESI): 495 (MH+).

Workup

  1. customEvaporation of solvent under high vacuum
  2. customgave a crude, which
  3. customwas purified by chromatography on silica gel eluting with EtOAc-hexane (1:1)

Sources & evidence

ORD record
ord-cc61170525ff44a4b95a0635f99fe5f6
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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