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Methyl chloroformate → HCID 70414805, compound

HRID 579759
Notes
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Reaction equation

HRID 579759 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.Cl[C:25]([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[Na+].[Na+].[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]\[C:38]([OH:40])=[O:39]>CN(C)C=O.C(O)C>[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]\[C:38]([OH:40])=[O:39].[CH3:28][O:27][C:25]([N:14]1[C:13]2[CH2:12][CH2:11][CH:10]([CH2:9][N:5]3[CH:6]=[CH:7][N:8]=[C:4]3[CH3:3])[C:22](=[O:23])[C:21]=2[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 444266Maleic AcidHCID 108912241,2,3,9-Tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one

Product 1

HCID 70414805HCID 70414805, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×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 at room temperature for 30 min. Methyl chloroformate (0.3 ml) was added and stirring continued at room temperature for 4 h. The resulting solution was basified with sodium carbonate (100 ml) filtered, and the filtrate was extracted with ethyl acetate (2×50 ml). The combined organic extracts and solid were washed with water (3×50 ml), dried (Na2SO4) and evaporated in vacuo to give a solid. Purification by flash chromatography (A) gave a solid, which was dissolved in ethanol (5 ml) and added to a solution of maleic acid (0.018 g) in ethanol (5 ml) to give the title compound (0.07 g) m.p. 91°-92°.

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 4 h
  3. filtrationfiltered
  4. extractionthe filtrate was extracted with ethyl acetate (2×50 ml)
  5. washThe combined organic extracts and solid were washed with water (3×50 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give a solid
  9. customPurification by flash chromatography (A)
  10. customgave a solid, which

Sources & evidence

ORD record
ord-6a7c0845b6894197b0a641754889d432
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