Methyl iodide → HCID 54298054, compound

HRID 436509Notes

Reaction equation

HRID 436509 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([CH:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:21])[CH:16]=3)[NH:11][C:10]=2[CH2:9]1)=[O:7])[CH3:4].[CH3:22]I>CN(C)C=O>[CH2:3]([O:5][C:6]([CH:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:21])[CH:16]=3)[N:11]([CH3:22])[C:10]=2[CH2:9]1)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 54455743HCID 54455743, compound

Product 1

HCID 54298054HCID 54298054, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 1.3 g. of 55 percent sodium hydride in mineral oil, 8 g. of 6-chloro-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid ethyl ester and 50 ml. of dimethylformamide was stirred at room temperature. After 1.5 hours all the sodium hydride had reacted and a solution of 4.5 g. of methyl iodide in 15 ml. of dimethylformamide was added. The mixture was stirred for 6 hours between 60°-65° C. Upon cooling to room temperature, the reaction mixture was concentrated to dryness under reduced pressure and the residue was partitioned between ether (200 ml.) and water (200 ml.). The ether phase was separated and washed by extraction with water (2 × 100 ml.). After the ether solution had dried over sodium sulfate, the desiccant was removed by filtration and the ether evaporated, yielding 7.2 g. of product. Following crystallization from methanol, 4.6 g. of 6-chloro-9-methyl-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid ethyl ester was obtained, m.p. 126°-127°.

Workup

  1. additionA mixture of 1.3 g
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  3. customthe residue was partitioned between ether (200 ml.) and water (200 ml.)
  4. customThe ether phase was separated
  5. washwashed by extraction with water (2 × 100 ml.)
  6. dry with materialAfter the ether solution had dried over sodium sulfate
  7. customthe desiccant was removed by filtration
  8. customthe ether evaporated
  9. customyielding 7.2 g
  10. customcrystallization from methanol, 4.6 g

Sources & evidence

ORD record
ord-0d0d8576074647b4a90c507cdec72731
Source dataset
uspto-grants-1977_02
Patent number
US04009181

Reaction notes

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