Dimethyl Disulfide → HCID 19864321, compound

HRID 1199923Notes

Reaction equation

HRID 1199923 reaction equation
C([Li])CCC.Br[C:7]1[S:23][C:10]2[CH:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][N:13]([CH3:16])[CH2:14][CH2:15][C:9]=2[CH:8]=1.[CH3:24][S:25]SC>CCCCCC.O1CCCC1>[CH3:16][N:13]1[CH2:14][CH2:15][C:9]2[CH:8]=[C:7]([S:25][CH3:24])[S:23][C:10]=2[CH:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]1

Participants

6

Reactant 3

HCID 12232Dimethyl DisulfideHCID 19864294HCID 19864294, compoundHCID 178418339Butyllithium

Product 1

HCID 19864321HCID 19864321, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of n-butyl lithium in n-hexane (1.6M, 0.75 ml) was added dropwise to a stirred solution of 2-bromo-6-methyl-8-phenyl-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine (0.40 g hydrobromide salt converted to free base by aqueous ammonia/dichloromethane extraction) in dry tetrahydrofuran (10 ml) cooled to -70° under nitrogen. After 10 minutes at -70° dimethyl disulphide (0.11 ml) was added dropwise and the mixture allowed to warm to room temperature. After 30 minutes the solution was evaporated, water (10 ml) added to the residue and extracted with dichloromethane (2×5 ml). The extracts were dried, filtered and evaporated to a pale yellow solid. Recrystallisation twice from n-hexane (4 ml) gave white needles (m.p. 90°) of the title product.

Workup

  1. temperaturecooled to -70° under nitrogen
  2. customAfter 30 minutes the solution was evaporated
  3. additionwater (10 ml) added to the residue
  4. extractionextracted with dichloromethane (2×5 ml)
  5. customThe extracts were dried
  6. filtrationfiltered
  7. customevaporated to a pale yellow solid
  8. customRecrystallisation twice from n-hexane (4 ml)

Sources & evidence

ORD record
ord-9330217efbde41d89185d3505136336f
Source dataset
uspto-grants-1990_02
Patent number
US04904653

Reaction notes

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