Hydrogen Bromide → HCID 19434010, compound

HRID 1736036Notes

Reaction equation

HRID 1736036 reaction equation
C[O:2][CH2:3][CH2:4][N:5]1[C:10]([CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:8]2[CH:18]=[C:19]([S:21]([NH2:24])(=[O:23])=[O:22])[S:20][C:7]=2[S:6]1(=[O:26])=[O:25].Br>O>[OH:2][CH2:3][CH2:4][N:5]1[C:10]([CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:8]2[CH:18]=[C:19]([S:21]([NH2:24])(=[O:23])=[O:22])[S:20][C:7]=2[S:6]1(=[O:25])=[O:26]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 19434082HCID 19434082, compound

Product 1

HCID 19434010HCID 19434010, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the product from Step A (1.56 g), 48% HBr(16 mL) and water (4 mL) was heated at reflux temperature for 18 h, evaporated to dryness, mixed with a saturated solution of sodium bicarbonate (60 mL) and extracted with ethyl acetate (2×80 mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by column chromatography (silica, 5% methanol/methylene chloride) to give a firm foam (0.85 g, 56%): mp 104°-108° C. Analysis. Calculated for C13H19N3O6S3 - 0.3H2O: C, 37.63; H, 4.76; N, 10.13. Found: C, 37.61; H, 4.60; N, 10.00.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 18 h
  3. customevaporated to dryness
  4. additionmixed with a saturated solution of sodium bicarbonate (60 mL)
  5. extractionextracted with ethyl acetate (2×80 mL)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customevaporated to a residue which
  8. customwas purified by column chromatography (silica, 5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-7ed55b7d0c7d4cfcaa735131dd41b719
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

Loading…