Sodium Sulfate → HCID 70406383, compound

HRID 414207Notes

Reaction equation

HRID 414207 reaction equation
[CH3:1][N:2]1[C@H:16]2[C:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)=[CH:5][C@H:4]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:3]1.S(Cl)([Cl:28])(=O)=O.[O-]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[Cl:28][C:13]1[NH:12][C:11]2[C:17]3[C:14]=1[CH2:15][C@@H:16]1[C:6]([C:7]=3[CH:8]=[CH:9][CH:10]=2)=[CH:5][C@H:4]([NH:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:23])[CH3:22])[CH2:3][N:2]1[CH3:1]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 24648Sulfuryl chlorideHCID 70406371HCID 70406371, compound

Product 1

HCID 70406383HCID 70406383, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2.0 g 6-methyl-8α-pivaloylamino-9,10-didehydro-ergoline, 100 ml CH2Cl2 and 50 mg silica gel is cooled to 0° and treated dropwise with 0.73 ml sulfurylchloride. The mixture is then stirred for 16 hours at room temperature, and then treated with 2N Na2SO4 and CH2Cl2. The organic phase is dried (Na2SO4), evaporated and chromatographed on 100 g silica gel using 8:2 CH2Cl2 /CH3OH. The title compound is obtained on crystallisaton from ether, m.p. 157°-160°.

Workup

  1. temperatureis cooled to 0°
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. customevaporated
  4. customchromatographed on 100 g silica gel using 8:2 CH2Cl2 /CH3OH

Sources & evidence

ORD record
ord-72f7aecaaec34bc69d145aae3c48c349
Source dataset
uspto-grants-1988_12
Patent number
US04791115

Reaction notes

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