Water → HCID 20205023, compound

HRID 978076Notes

Reaction equation

HRID 978076 reaction equation
[CH3:1][N:2]([CH3:17])[C:3](=[S:16])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:6]=1[C:12]([O:14][CH3:15])=[O:13].[H-].[Na+].I[CH3:21].O>CN(C)C=O>[CH3:17][N:2]([CH3:1])[C:3](=[S:16])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:21])[C:6]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53753980HCID 53753980, compound

Product 1

HCID 20205023HCID 20205023, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of O-2-carbomethoxy-3-hydroxyphenyl dimethylthiocarbamate (1.0 g, 3.9 mmol) in N,N-dimethylformamide (10 ml) was added dropwise with stirring to a suspension of sodium hydride (0.19 g, 3.9 mmol) in N,N-dimethylformamide (15 ml) cooled to 0° C. in an ice bath. The reaction mixture was stirred for 1 hour at room temperature. Iodomethane (0.26 ml, 4.3 mmol) was added, and stirring was continued for an additional 3 hours, at which time the mixture was poured into water. Extraction with diethyl ether followed by washing of the extracts with water (3×), saturated aqueous sodium chloride solution, drying (sodium sulfate), and evaporation gave a syrup that was triturated with methanol to afford O-2-carbomethoxy-3-methoxyphenyl dimethylthiocarbamate as a white crystalline solid; yield 0.80 g (76%). NMR (CDCl3, 60 MHz: δ3.30 (d, NME2) p.p.m.

Workup

  1. stirringstirring
  2. waitwas continued for an additional 3 hours, at which time
  3. extractionExtraction with diethyl ether
  4. washby washing of the extracts with water (3×), saturated aqueous sodium chloride solution
  5. customdrying
  6. custom(sodium sulfate), and evaporation
  7. customgave a syrup that
  8. customwas triturated with methanol

Sources & evidence

ORD record
ord-0bb25974c1984b6fa32cc0cd486d187f
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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