Dimethylformamide → HCID 19864322, compound

HRID 1199919Notes

Reaction equation

HRID 1199919 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[CH2:13][CH2:12][C:11]2[CH:14]=[CH:15][S:16][C:10]=2[CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8]1.CN(C)[CH:25]=[O:26]>>[CH3:6][N:7]1[CH2:13][CH2:12][C:11]2[CH:14]=[C:15]([CH:25]=[O:26])[S:16][C:10]=2[CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 19864284HCID 19864284, compound

Product 1

HCID 19864322HCID 19864322, compound

Procedure

Phosphorous oxychloride (4.6 ml) was added dropwise to a stirred solution of 6-methyl-8-phenyl-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine (3.98 g) in dimethylformamide (17 ml) cooled in an ice bath. The mixture was heated to 60° for 18 hours and then evaporated. The residue was dissolved in iced water (50 ml), basified with 2M sodium hydroxide to pH~12 and extracted with dichloromethane (2×100 ml). The extracts were dried, filtered and evaporated to a brown oil. Crystallisation from hexane gave the title product as yellow crystals (m.p. 88°).

Workup

  1. temperaturecooled in an ice bath
  2. temperatureThe mixture was heated to 60° for 18 hours
  3. customevaporated
  4. dissolutionThe residue was dissolved in iced water (50 ml)
  5. extractionextracted with dichloromethane (2×100 ml)
  6. customThe extracts were dried
  7. filtrationfiltered
  8. customevaporated to a brown oil
  9. customCrystallisation from hexane

Sources & evidence

ORD record
ord-e7e52724f0254c2198fb4a43f2c25134
Source dataset
uspto-grants-1990_02
Patent number
US04904653

Reaction notes

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