Dimethyl Disulfide → HCID 10358295, compound

HRID 2413904Notes

Reaction equation

HRID 2413904 reaction equation
S(Cl)(Cl)(=O)=O.CS[S:8][CH3:9].C(SCl)C.[CH3:14][C@@H:15]1[CH2:29][C@H:28]2[C@@H:18]([CH2:19][C:20]3[C:30]4[C:23](=[CH:24][CH:25]=[CH:26][C:27]2=4)[NH:22][CH:21]=3)[N:17]([CH2:31][CH2:32][CH3:33])[CH2:16]1>ClCCl>[CH3:14][C@@H:15]1[CH2:29][C@H:28]2[C@@H:18]([CH2:19][C:20]3[C:30]4[C:23](=[CH:24][CH:25]=[CH:26][C:27]2=4)[NH:22][C:21]=3[S:8][CH3:9])[N:17]([CH2:31][CH2:32][CH3:33])[CH2:16]1

Participants

6

Reactant 4

HCID 12232Dimethyl DisulfideHCID 24648Sulfuryl chlorideHCID 12275523ethanesulfenyl chlorideHCID 58607200HCID 58607200, compound

Product 1

HCID 10358295HCID 10358295, 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 ethyl sulphenyl chloride was added dropwise to a suspension of 8β-methyl-6-propylergoline (2.4 g), in dichloromethane (150 ml) at -70° C. The reaction mixture was stirred and allowed to reach room temperature overnight. Ice 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 (CH2CH2) and crystallisation from ethanol gave the title compound. The free base was converted to its maleate salt and crystallised from ethanol, m.p. 216°-219° C.

Workup

  1. customto reach room temperature
  2. additionIce cold ammonia solution was added
  3. extractionthe mixture extracted with dichloromethane (3×100 ml)
  4. washThe combined extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness
  7. customChromatography on neutral alumina (CH2CH2) and crystallisation from ethanol

Sources & evidence

ORD record
ord-978c809c62a64361bec4df260388a03b
Source dataset
uspto-grants-1988_01
Patent number
US04720498

Reaction notes

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