Hydrochloric Acid → HCID 19024930, compound

HRID 1033825Notes

Reaction equation

HRID 1033825 reaction equation
[CH2:1]([S:8][C:9]([CH3:24])([CH3:23])[CH2:10][N:11]([CH2:17][CH2:18][P:19]([CH3:22])([CH3:21])=[S:20])[C:12](=O)[CH2:13][O:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1(C)C=CC=CC=1.O1CCCC1>[CH3:22][P:19]([CH3:21])([CH2:18][CH2:17][N:11]([CH2:10][C:9]([S:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:24])[CH3:23])[CH2:12][CH2:13][O:14][CH3:15])=[S:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19024942HCID 19024942, compound

Product 1

HCID 19024930HCID 19024930, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-(2-benzylthio-2-methylpropyl)-N-(2-dimethylphosphinothioylethyl)methoxyacetamide (750 mg) in dry toluene (10 cm3) at 0° C., under an atmosphere of dry nitrogen was added a solution of boranetetrahydrofuran complex in tetrahydrofuran (5.25 cm3, 1M). The mixture was stirred for 30 min at 0° C. and then for 4 h at room temperature. Concentrated hydrochloric acid (1 cm3) was added carefully and the tetrahydrofuran then removed under reduced pressure. The remaining aqueous solution was made strongly basic by the addition of aqueous sodium hydroxide (6M) and then extracted with chloroform (3×10 cm3). The extracts were dried (Na2SO4) and the solvent removed to give the product (500 mg, 71%) as a yellow oil.

Workup

  1. waitfor 4 h at room temperature
  2. customthe tetrahydrofuran then removed under reduced pressure
  3. additionThe remaining aqueous solution was made strongly basic by the addition of aqueous sodium hydroxide (6M)
  4. extractionextracted with chloroform (3×10 cm3)
  5. dry with materialThe extracts were dried (Na2SO4)
  6. customthe solvent removed

Sources & evidence

ORD record
ord-7f7168d9cbdc4eb984268a6c18ed832e
Source dataset
uspto-grants-1994_05
Patent number
US05312904

Reaction notes

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