Acetonitrile → (NZ)-N-[5-methylidene-3-(2,2,3,3-tetrafluoro-1,4-benzodioxin-6-yl)-1,3-thiazolidin-2-ylidene]imidazole-1-carboxamide

HRID 1260360Notes

Reaction equation

HRID 1260360 reaction equation
[CH2:1]=[C:2]1[S:6][C:5](=[NH:7])[N:4]([C:8]2[CH:21]=[CH:20][C:11]3[O:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[O:15][C:10]=3[CH:9]=2)[CH2:3]1.C([N:25]([CH:28](C)C)CC)(C)C.[C:31](C1NC=CN=1)(C1NC=CN=1)=[O:32].[C:43](#[N:45])[CH3:44]>>[CH2:1]=[C:2]1[S:6]/[C:5](=[N:7]\[C:31]([N:45]2[CH:43]=[CH:44][N:25]=[CH:28]2)=[O:32])/[N:4]([C:8]2[CH:21]=[CH:20][C:11]3[O:12][C:13]([F:19])([F:18])[C:14]([F:16])([F:17])[O:15][C:10]=3[CH:9]=2)[CH2:3]1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 866191675-Methylene-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazolidin-2-imine

Product 1

HCID 87463827(NZ)-N-[5-methylidene-3-(2,2,3,3-tetrafluoro-1,4-benzodioxin-6-yl)-1,3-thiazolidin-2-ylidene]imidazole-1-carboxamide

Conditions

Temperature
80 °C

Procedure

The crude imine (Example 22C, 169 mg, <0.52 mmol) was dissolved into acetonitrile (10 mL), treated with diisopropylethylamine (130 μL, 0.75 mmol) and carbonyl diimidazole (94 mg, 0.58 mmol), and then heated near 80° C. overnight. The mixture was concentrated and chromatographed through silica (Oct. 40, 1950 to 25/25/50% EtOAc/CH2Cl2/hexanes) to give the titled compound. 1H NMR (300 MHz, CDCl3) δ ppm 4.83 (2 H), 5.42 (1 H), 5.45 (1 H), 7.01 (1 H), 7.26-7.35 (3 H), 7.44 (1 H), 8.10 (1 H); MS (ESI) m/z 415 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed through silica (Oct. 40, 1950 to 25/25/50% EtOAc/CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-633e8281ae4f4426b5faaf25c4652f8b
Source dataset
uspto-grants-2013_06
Patent number
US08470813B2

Reaction notes

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