Bromine → HCID 19864333, compound

HRID 1199921Notes

Reaction equation

HRID 1199921 reaction equation
[Br:1]Br.[OH:3][CH2:4][C:5]1[S:21][C:8]2[CH:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][N:11]([CH3:14])[CH2:12][CH2:13][C:7]=2[CH:6]=1.O.O.O.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:1][C:6]1[C:7]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[S:21][C:5]=1[CH2:4][OH:3]

Participants

5

Reactant 3

HCID 24408BromineHCID 19864317HCID 19864317, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 19864333HCID 19864333, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (0.23 ml) was added dropwise to a stirred solution of 2-hydroxymethyl-6-methyl-8-phenyl-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine (1.20 g) and sodium acetate trihydrate (1.8 g) in acetic acid (60 ml) at room temperature. After 1 hour the solution was evaporated, the residue dissolved in water (100 ml), basified to pH~11 with 0.880 ammonia solution and extracted with dichloromethane (2×100 ml). The extracts were dried, filtered and evaporated to a brown oil (1.74 g). Chromatography on silica, eluting with 2% methanol in dichloromethane gave a solid (0.80 g) which was recrystallised from toluene (15 ml) to give the title product (m.p. 141°).

Workup

  1. customAfter 1 hour the solution was evaporated
  2. dissolutionthe residue dissolved in water (100 ml)
  3. extractionextracted with dichloromethane (2×100 ml)
  4. customThe extracts were dried
  5. filtrationfiltered
  6. customevaporated to a brown oil (1.74 g)
  7. washChromatography on silica, eluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-2d34ded1fefb41989b12122481a19f7e
Source dataset
uspto-grants-1990_02
Patent number
US04904653

Reaction notes

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