Methanol → HCID 71087465, compound

HRID 927375Notes

Reaction equation

HRID 927375 reaction equation
C[N:2](C)[C:3](=[N:5][C:6](=[S:18])[C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:9])[CH3:8])[CH3:4].NOS(O)(=O)=O.N1C=CC=CC=1.CO>C(O)C>[CH3:4][C:3]1[N:5]=[C:6]([C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:9])[CH3:8])[S:18][N:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 76284hydroxylamine-O-sulfonic acidHCID 86674739HCID 86674739, compound

Product 1

HCID 71087465HCID 71087465, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 1-(1-(dimethylamino)ethylideneamino)-2-methyl-1-thioxopropan-2-ylcarbamate (2.9 g, 10 mmol), hydroxylamine-O-sulfonic acid (CAN 2950-43-8, 1.37 g, 12 mmol), pyridine (1.6 g, 20.2 mmol) and methanol (4 mL) in ethanol (20 mL) was stirred at room temperature for 2 h. After evaporation of solvents, the residue was diluted with ethyl acetate (40 mL) and water (40 mL). The organic layer was washed with brine (40 mL), dried over anhydrous sodium sulfate and concentrated to give crude product (2.5 g, 96%) as yellow oil. The product was used directly in the next step without further purification; MS (EI): m/e 258.2 [M+H]+.

Workup

  1. customAfter evaporation of solvents
  2. additionthe residue was diluted with ethyl acetate (40 mL) and water (40 mL)
  3. washThe organic layer was washed with brine (40 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0f2f1b55978b44f9a282793074d2c705
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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