Ammonia → HCID 18631500, compound

HRID 1195072Notes

Reaction equation

HRID 1195072 reaction equation
C[Si](C)(C)[I:3].[OH:6][CH2:7][C@@H:8]1[CH:23]=[C:22]2[C@@H:12]([CH2:13][C:14]3[C:24]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]2=4)[NH:16][CH:15]=3)[N:10]([CH3:11])[CH2:9]1.O.N>CS(C)=O>[I:3][C:15]1[NH:16][C:17]2[C:24]3[C:14]=1[CH2:13][C@@H:12]1[C:22]([C:21]=3[CH:20]=[CH:19][CH:18]=2)=[CH:23][C@@H:8]([CH2:7][OH:6])[CH2:9][N:10]1[CH3:11]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 149871413-67-8HCID 85247Trimethylsilyl iodide

Product 1

HCID 18631500HCID 18631500, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

2.3 g of trimethyliodosilane are portionwise added to 20 ml of dimethylsulfoxide and the mixture is stirred at room temperature for 5 minutes. Then, a solution of 1 g of lysergol in 15 ml of dimethylsulfoxide is added, the reaction mixture is stirred for 15 minutes, then poured into water and made alkaline by adding aqueous ammonia up to a pH value of 8 to 9. The precipitate is filtered off, wash 3 times with 20 ml of water each and dried to give the title compound in a yield of 1.1 g (0.002913, mole, 74%).

Workup

  1. stirringthe reaction mixture is stirred for 15 minutes
  2. filtrationThe precipitate is filtered off
  3. washwash 3 times with 20 ml of water each and
  4. customdried

Sources & evidence

ORD record
ord-ca11a33b4e5d4e489de2d8c867fd5cf3
Source dataset
uspto-grants-1989_03
Patent number
US04816587

Reaction notes

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