Water → HCID 178460709, compound

HRID 621819Notes

Reaction equation

HRID 621819 reaction equation
[Br:1]Br.[CH:3]([S:6][C:7]1[CH:11]=[C:10]([Si](C)(C)C)[O:9][C:8]=1[C:16]([NH:18][C:19]1[NH:23][N:22]=[N:21][N:20]=1)=[O:17])([CH3:5])[CH3:4].O>C(Cl)(Cl)Cl.C(O)(=O)C>[Br:1][C:10]1[O:9][C:8]([C:16]([NH:18][C:19]2[NH:23][N:22]=[N:21][N:20]=2)=[O:17])=[C:7]([S:6][CH:3]([CH3:5])[CH3:4])[CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 178460744HCID 178460744, compound

Product 1

HCID 178460709HCID 178460709, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of 3.1 g (19.5 mmol, 1.6 equiv) of bromine in 7 mL of chloroform is added dropwise to a room temperature solution of 3.98 g (12.22 mmol) of 3-isopropylthio-5-trimethylsilyl-N-1H-tetrazol-5-yl-2-furancarboxamide in 13 mL of chloroform and 20 mL of glacial acetic acid under nitrogen atmosphere. The resulting mixture is stirred at room temperature for 23 hours then poured onto 200 mL of water. The aqueous mixture is extracted with ethyl acetate (3x). The combined extracts are washed with 10% aqueous sodium thiosulfate and saturated aqueous sodium chloride, dried over sodium sulfate and concentrated in vacuo to give a yellow solid. Recrystallization from isopropanol/water gave 1.58 g (4.06 g theo., 38%) of the desired product as a yellow solid; mp 200°-210° C. (dec).

Workup

  1. extractionThe aqueous mixture is extracted with ethyl acetate (3x)
  2. washThe combined extracts are washed with 10% aqueous sodium thiosulfate and saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a yellow solid
  6. customRecrystallization from isopropanol/water

Sources & evidence

ORD record
ord-9ae3adf308434b7d838f00eab21720b1
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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