Methane → HCID 20326609, compound

HRID 918484Notes

Reaction equation

HRID 918484 reaction equation
[H-].[Na+].[S:3]1[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7]=2[C:6](=[O:16])[CH:5]=[CH:4]1.[CH3:17][N:18]([CH2:20][CH2:21][CH2:22][Cl:23])[CH3:19].C.[OH-].[Na+]>CN(C)C=O>[ClH:23].[CH3:17][N:18]([CH3:19])[CH2:20][CH2:21][CH2:22][N:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[C:15]2[S:3][CH:4]=[CH:5][C:6](=[O:16])[C:7]1=2

Participants

7

Reactant 5

HCID 297MethaneHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 20326608Thiopyrano[3,2-b]indol-4(5H)-one

Product 1

HCID 20326609HCID 20326609, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.3 g (0.055 mole) of 50% sodium hydride in mineral oil, 50 ml of dimethylformamide (DMF) and 10.0 g (.05 mole) of thiopyrano [3,2-b]indol-4(5H)-one is stirred for 3 hours, then 12.2 g (0.1 mole) of dimethylamino-propylchloride is added. Stirring is continued for 20 hours at 95°, then the mixture is poured onto ice containing conc. HCl. The cloudy solution is clarified with charcoal, made basic with 20% sodium hydroxide solution, and the precipitated oil extracted with ether. The ether is dried, and dry HCl passed in. The precipitated salt weighed 10.1 g and is recrystallized from isopropanol, mp 226°-228°C.

Workup

  1. stirringStirring
  2. waitis continued for 20 hours at 95°
  3. additionthe mixture is poured onto ice containing conc. HCl
  4. extractionthe precipitated oil extracted with ether
  5. dry with materialThe ether is dried
  6. customis recrystallized from isopropanol, mp 226°-228°C.

Sources & evidence

ORD record
ord-e78ca8ab5f1f47d78a2cd7c65cade4a5
Source dataset
uspto-grants-1976_07
Patent number
US03971806

Reaction notes

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