Ammonia → HCID 9864683, compound

HRID 2413902Notes

Reaction equation

HRID 2413902 reaction equation
S(Cl)(Cl)(=O)=O.CS[S:8][CH3:9].CSCl.[CH3:13][N:14]1[C@H:28]2[C@@H:18]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:29]=3[C:26]([CH2:27]2)=[CH:25][NH:24]4)[CH:17]=[C:16]([CH3:30])[CH2:15]1.N>ClCCl>[CH3:13][N:14]1[C@H:28]2[C@@H:18]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:29]=3[C:26]([CH2:27]2)=[C:25]([S:8][CH3:9])[NH:24]4)[CH:17]=[C:16]([CH3:30])[CH2:15]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 12232Dimethyl DisulfideHCID 24648Sulfuryl chlorideHCID 73484548-42-5HCID 138595Methanesulfenylchloride

Product 1

HCID 9864683HCID 9864683, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of sulphuryl chloride (0.74 g,) in dichloromethane (15 ml) was added dropwise over 15 minutes at -20° C. to a stirred solution of dimethyl disulphide (0.46 g), in dichloromethane (15 ml). After allowing it to reach room temperature the solution of methyl sulphenyl chloride was added dropwise to a suspension of 8,9-didehydro-6,8-dimethylergoline (2.4 g) in dichloromethane (150 ml) at -70° C. The reaction mixture was stirred and allowed to reach room temperature overnight. Cold ammonia solution was added and the mixture extracted with dichloromethane (3×100 ml). The combined extracts were washed with water, dried (MgSO4) and evaporated to dryness. Chromatography on neutral alumina (CH2Cl2) and crystallisation from cyclohexane gave the title compound, m.p. 148°-150° C. The mesylate was also prepared, m.p. 220°-222° C.

Workup

  1. customto reach room temperature
  2. extractionthe mixture extracted with dichloromethane (3×100 ml)
  3. washThe combined extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customChromatography on neutral alumina (CH2Cl2) and crystallisation from cyclohexane

Sources & evidence

ORD record
ord-747701b5c8c646f78a155460ccd0f35e
Source dataset
uspto-grants-1988_01
Patent number
US04720498

Reaction notes

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