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Sodium hydride → HCID 70414521, compound

HRID 579758
Notes
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Reaction equation

HRID 579758 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:5]([CH2:9][CH:10]2[C:22](=[O:23])[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][C:13]=3[CH2:12][CH2:11]2)[CH:6]=[CH:7][N:8]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33]>CN(C)C=O.C(O)C.CCOCC>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33].[CH3:3][C:4]1[N:5]([CH2:9][CH:10]2[C:22](=[O:23])[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]([S:25]([CH3:24])(=[O:27])=[O:26])[C:13]=3[CH2:12][CH2:11]2)[CH:6]=[CH:7][N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 444266Maleic AcidHCID 108912241,2,3,9-Tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one

Product 1

HCID 70414521HCID 70414521, compound

Reagents, catalysts & solvents 3

HCID 702
Ethanol
Solvent
2×
HCID 3283Diethyl EtherSolvent
HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.075 g) was added to a solution of 1,2,3,9-tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one (0.7 g) in dimethylformamide (10 ml) and the mixture was stirred for 30 min. Methanesulphonyl chloride (0.25 ml) was added and stirring continued at room temperature for 5 h. The resulting solution was partitioned between sodium carbonate (100 ml) and ethyl acetate (3×50 ml). The combined organic layers were washed with water (3×50 ml), dried (Na2SO4), and evaporated in vacuo to give an oil. Purification by flash chromatography (A) gave an oil, which was dissolved in ethanol (10 ml) and added to a solution of maleic acid (0.15 g) in ethanol (5 ml). Addition of dry ether precipitated the title compound (0.7 g) m.p. 141°-142.5°.

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 5 h
  3. customThe resulting solution was partitioned between sodium carbonate (100 ml) and ethyl acetate (3×50 ml)
  4. washThe combined organic layers were washed with water (3×50 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customto give an oil
  8. customPurification by flash chromatography (A)
  9. customgave an oil, which
  10. customprecipitated the title compound (0.7 g) m.p. 141°-142.5°

Sources & evidence

ORD record
ord-c6e5fd534fe44bf9a4f00cf265bd1176
Source dataset
uspto-grants-1988_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04749718

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes