Methanol → HCID 22414561, compound

HRID 1721314Notes

Reaction equation

HRID 1721314 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[S:10])[NH2:9])=[CH:4][C:3]=1[CH3:11].NOS(O)(=O)=O.CO.[N:20]1C=CC=[CH:22][CH:21]=1>COC(OC)(N(C)C)C.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:10][N:20]=[C:21]([CH3:22])[N:9]=2)=[CH:4][C:3]=1[CH3:11]

Participants

7

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 76284hydroxylamine-O-sulfonic acidHCID 2183382941963-21-7

Product 1

HCID 22414561HCID 22414561, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 878351,1-Dimethoxyethyl(dimethyl)amineSolvent

Procedure

A solution of 4-bromo-3-methylbenzenecarbothioamide (1.20 g) in dimethylacetamide dimethyl acetal (2 ml) and dichloromethane (30 ml) was stirred under nitrogen at room temperature for 7 h. The solvent was evaporated in vacuo to give a dark brown oil to which was added hydroxylamine-O-sulphonic acid (0.88 g), methanol (20 ml) and pyridine (0.83 ml) and the mixture stirred at room temperature under nitrogen for 16 h. After evaporation, aqueous potassium carbonate was added and the mixture was extracted with dichloromethane. The combined extracts were dried and evaporated to give a brown residue which was purified by column chromatography on silica eluting with hexane:ethyl acetate (4:1) to give the title compound as an orange solid (0.8 g). T.l.c.hexane:ethyl acetate (4:1), Rf=0.52

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give a dark brown oil to which
  3. customAfter evaporation, aqueous potassium carbonate
  4. additionwas added
  5. extractionthe mixture was extracted with dichloromethane
  6. customThe combined extracts were dried
  7. customevaporated
  8. customto give a brown residue which
  9. customwas purified by column chromatography on silica eluting with hexane:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-3273824991e94518be246d9bae1b3b69
Source dataset
uspto-grants-1996_04
Patent number
US05510350

Reaction notes

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