Sodium hydride → HCID 67564508, compound

HRID 964560Notes

Reaction equation

HRID 964560 reaction equation
[CH3:1][C:2]1[C:3]([C:19]([OH:21])=O)=[N:4][C:5]2[C:17]=1[C:16]([CH3:18])=[C:15]1[C:7](=[N:8][C:9]3[C:14]1=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=2.[C:22]([C:29]1NC=CN=1)([C:24]1[NH:25]C=C[N:28]=1)=O.[H-].[Na+]>O1CCCC1>[CH3:1][C:2]1[C:3]([C:19]2[O:21][N:28]=[C:24]([CH2:22][CH3:29])[N:25]=2)=[N:4][C:5]2[C:17]=1[C:16]([CH3:18])=[C:15]1[C:7](=[N:8][C:9]3[C:14]1=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 19077459HCID 19077459, compound

Product 1

HCID 67564508HCID 67564508, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

3,4-Dimethylpyrrolo[2,3-b]carbazole-2-carboxylic acid (0.49 g, 1.76 mmol) and carbonyl diimidazole (0.33 g, 1.94 mmol) were dissolved in freshly distilled tetrahydrofuran (10 ml) in an oven-dried flask under a nitrogen atmosphere and this solution was stirred at room temperature for three hours. Meanwhile, in a second oven-dried flask, ethylamidoxime (0.39 g 4.43 mmol) was dissolved in THF (5 ml). To this was added crushed 3 Å sieves and the mixture was stirred at room temp for 45 min. Sodium hydride (60% dispersion in mineral oil, 0.142 g, 3.5 mmol) was added and the mixture stirred for a further 2.5 hours. The contents of the two flasks were combined (with further 10 ml THF) and stirred at room temp for 18 hours, by which time TLC showed complete consumption of the imidazolide intermediate. The solvent was removed in vacuo to give a yellow solid. Chromatography on silica (eluting with 25% ethyl acetate/hexane) gave the title compound as a yellow solid (0.150 g, 26%) with m.p. 258°-260° C. (decomp.). (Found: C, 72.03; H, 5.28; N, 16.42. C20H18N4O 0.08EtOAC requires: C, 72.33; H, 5.57; N, 16.60%); δH [2H6 ]-DMSO 11.55 (1H, s, 1-NH), 10.94 (1H, s, 9NH), 8.19 (1H, d, J 7.5, 5-H), 7.29-7.43 (2H, m, 7-H, 8-H), 7.22 (1H, s, 10-H), 7.13 (1H, ddd, J 8, 5.5, 2, 6-H), 3.20 and 3.03 (2×3H, 2×s, 3--CH3 and 4--CH3), 2.83 (2H, q, 7.5, CH2 CH3), 1.37 (3H, t, 7.5, CH2CH3); m/z (%) 330 (100, M+), 260 (34), 232 (29); νmax (KBr disk)/cm-1 3394, 1599, 1259.

Workup

  1. additionTo this was added
  2. customcrushed 3 Å sieves
  3. stirringthe mixture was stirred at room temp for 45 min
  4. stirringthe mixture stirred for a further 2.5 hours
  5. stirringstirred at room temp for 18 hours, by which time TLC
  6. customconsumption of the imidazolide intermediate
  7. customThe solvent was removed in vacuo
  8. customto give a yellow solid

Sources & evidence

ORD record
ord-640c330ff726425ebc2fa68d8544024b
Source dataset
uspto-grants-1998_06
Patent number
US05770598

Reaction notes

Loading…