Ammonia → HCID 14676871, compound

HRID 1165579Notes

Reaction equation

HRID 1165579 reaction equation
N.[CH3:2][NH:3][CH2:4][CH:5]1[C:10]2[N:11](CC3C=CC=CC=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:9]=2[S:8][CH2:7][CH2:6]1.[Na].[Cl-].[NH4+]>CCOCC>[CH3:2][NH:3][CH2:4][CH:5]1[C:10]2[NH:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:9]=2[S:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 12803591HCID 12803591, compound

Product 1

HCID 14676871HCID 14676871, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-70 °C

Procedure

Liquid ammonia (ca. 100 ml) is trapped in a solution of 4-methylaminomethyl-5-benzyl-2,3,4,5-tetrahydrothiopyrano[3,2-b]indole (1.6 g) in ether (20 ml) under cooling at -70° C. A piece of sodium metal is added occasionally under refluxing. The refluxing is continued for 1.5 hours after the dark green color of the reaction mixture disappears. The reaction mixture is neutralized with ammonium chloride, the excess ammonia removed, and then the residue extracted with methylene chloride after addition of water. The extract is washed with water, dried and evaporated to give the title compound (1.06 g): Yield 91.4%. Recrystallization from benzene-petroleum benzine gives crystals melting at 100°-101° C.

Workup

  1. temperatureunder refluxing
  2. customthe excess ammonia removed
  3. extractionthe residue extracted with methylene chloride
  4. additionafter addition of water
  5. washThe extract is washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-00b7bbb5011141a48078202243f2b0c1
Source dataset
uspto-grants-1990_03
Patent number
US04910318

Reaction notes

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