Sodium hydride → HCID 19077470, compound

HRID 964561Notes

Reaction equation

HRID 964561 reaction equation
[CH3:1][C:2]1[C:3]([C:19](O)=[O:20])=[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](C1NC=CN=1)([C:24]1[NH:25]C=C[N:28]=1)=O.[N-]1C=CN=C1.[H-].[Na+]>O1CCCC1>[CH3:1][C:2]1[C:3]([C:19]2[O:20][N:28]=[C:24]([CH3:22])[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:10]1=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:6]=2

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 3386966ImidazolateHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 19077459HCID 19077459, compound

Product 1

HCID 19077470HCID 19077470, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,4-Dimethylpyrrolo[2,3-b]carbazole-2-carboxylic acid (0.5 g, 1.8 mmol) and carbonyl diimidazole (0.34 g, 2 mmol) were dissolved in freshly distilled tetrahydrofuran (20 ml) in an oven-dried flask under a nitrogen atmosphere. The resulting orange solution was stirred at room temperature for two hours, by which time it was an orange suspension, and complete conversion of the acid to the imidazolide intermediate was verified by TLC. Meanwhile, in a second oven-dried flask, methylamidoxime (0.27 g, 3.6 mmol) was dissolved in THF (10 ml). To this was added crushed 3 Å sieves and the mixture was stirred at room temp for 45 mins. Sodium hydride (60% dispersion in mineral oil, 0.243 g, 6.12 mmol) was added and the mixture stirred for a further 2 hours. The contents of the two flasks were combined 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 ethyl acetate/hexane 1:2) gave the pure yellow product (0.044 g, 8%) with m.p. 248°-249° C. (Found: C, 71.97; H, 5.07; N, 17.21. C19H16N4O.0.05EtOAc requires: C, 71.89; H. 5.15; N, 17.47%); δH [2H6 ]-DMSO 11.54 (1H s, 1-NH), 10.92 (1H, s, 9-NH), 8.17 (1H, d, J 7.5, 5-H), 7.41-7.28 (2H, m, 7-H, 8-H), 7.19 (1H, s, 10-H), 7.16-7.06 (1H, m, 6-H), 3.18 and 3.00 (2×3H, 2×s, 3-CH3 and 4-CH3), 2.43 (3H, s, 3'-CH3); m/z (%) 316 (100, M+), 260 (19), 232 (31).

Workup

  1. additionTo this was added
  2. customcrushed 3 Å sieves
  3. stirringthe mixture was stirred at room temp for 45 mins
  4. stirringthe mixture stirred for a further 2 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-6800177b15ae4deaa4e9f98640535239
Source dataset
uspto-grants-1998_06
Patent number
US05770598

Reaction notes

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