Dimethylformamide → HCID 54351672, compound

HRID 127523Notes

Reaction equation

HRID 127523 reaction equation
CN([CH2:4][CH:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[S:8][CH2:7][CH2:6]1)C.[H-].[Na+].[C:20](Cl)(=[O:22])[CH3:21].[Cl-].[NH4+].[CH3:26][N:27]([CH3:30])[CH:28]=O>>[C:20]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]2[CH:5]([CH2:4][CH2:26][N:27]([CH3:30])[CH3:28])[CH2:6][CH2:7][S:8][C:9]1=2)(=[O:22])[CH3:21]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 3056094N,N-Dimethyl-1-(2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-4-yl)methanamine

Product 1

HCID 54351672HCID 54351672, compoundYield 84%

Conditions

Temperature
40 °C

Procedure

To a solution of 4-dimethylaminomethyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole (246 mg) in dimethylformamide (4 ml) is added a 50% suspension (72 mg) of sodium hydride in mineral oil. The mixture is stirred at 40° C. for 30 minutes and further at room temperature for 1 hour after addition of acetyl chloride (95 mg) under ice-cooling and a cold aqueous solution of ammonium chloride is added thereto followed by extraction with chloroform. The extract is washed with water, dried and evaporated. The residue is washed with pentane to give crystals of the title compound (244 mg) melting at 131°-133° C. Yield: 84%

Workup

  1. temperaturecooling
  2. extractionthereto followed by extraction with chloroform
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. washThe residue is washed with pentane

Sources & evidence

ORD record
ord-59fd3c0dd4fe4df3ac288beabfaa8442
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Reaction notes

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