Formaldehyde → HCID 9972946, compound

HRID 2413905Notes

Reaction equation

HRID 2413905 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[C:13]([S:18][CH3:19])[NH:12]4)[CH:5]=[C:4]([CH3:20])[CH2:3]1.[OH2:21].[CH2:22]=O>>[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[C:13]([S:18][CH3:19])[N:12]4[CH2:22][OH:21])[CH:5]=[C:4]([CH3:20])[CH2:3]1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 9864683HCID 9864683, compound

Product 1

HCID 9972946HCID 9972946, compound

Procedure

A solution of 8,9-didehydro-6,8-dimethyl-2-methylthio ergoline (see Example 1) (2.84 g) in aqueous formaldehyde (40%, 35 ml) was refluxed for 2 hours. On cooling, water (100 ml) was added and the solution extracted several times with ethyl acetate. The organic extracts were collected, washed with water, dried over anhydrous magnesium sulphate and the solution filtered. It was reduced in vacuo to give a yellow oil which solidified on standing (2.2 g). This was passed through a dry neutral alumina column (100 g), eluting with chloroform and the final product, 8,9-didehydro-6,8-dimethyl-1-hydroxymethyl-2-methyl thioergoline recyrstallised from acetonitrile, m.p. 133°-135°.

Workup

  1. temperatureOn cooling
  2. extractionthe solution extracted several times with ethyl acetate
  3. customThe organic extracts were collected
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationthe solution filtered
  7. customto give a yellow oil which
  8. washeluting with chloroform

Sources & evidence

ORD record
ord-5037daa1841e4ba7b4d17aad4167580b
Source dataset
uspto-grants-1988_01
Patent number
US04720498

Reaction notes

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