Methyl Isocyanate → HCID 54101491, compound

HRID 1076406Notes

Reaction equation

HRID 1076406 reaction equation
[N:1](=[C:3]1[C:8]([CH3:10])([CH3:9])[S:7][CH2:6][CH2:5][O:4]1)[OH:2].[CH3:11][N:12]=[C:13]=[O:14].C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC>CCOCC>[CH3:11][NH:12][C:13]([O:2][N:1]=[C:3]1[C:8]([CH3:10])([CH3:9])[S:7][CH2:6][CH2:5][O:4]1)=[O:14]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 9798523Di-n-butyl diacetoxy tinHCID 73795642HCID 73795642, compound

Product 1

HCID 54101491HCID 54101491, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherCatalyst

Procedure

A quantity of 3.2 grams of crude 2-oximino-3,3-dimethyl-1,4-oxathiane was caused to react with 4 ml of methyl isocyanate in 75 ml of ether containing 5 drops of dibutyltin diacetate at room temperature for twenty hours. The excess methyl isocyanate and solvent were evaporated, and the residue taken up in ethyl acetate. After rinsing this solution with 100 ml of saturated brine and back-extraction with 100 ml of ethyl acetate, the combined organic solutions were dried over magnesium sulfate, filtered, and the solvent evaporated. The resulting thick oil was triturated with about 30 ml of a 3:1 isopropyl ether/ethyl acetate mixture at room temperature. Filtration afforded 0.7 g of pure 2-(methylcarbamoyloximino)-3,3-dimethyl-1,4-oxathiane, mp 67.0°-68.0°; structure confirmed by spectral analysis.

Workup

  1. customThe excess methyl isocyanate and solvent were evaporated
  2. washAfter rinsing this solution
  3. extractionwith 100 ml of saturated brine and back-extraction with 100 ml of ethyl acetate
  4. dry with materialthe combined organic solutions were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe resulting thick oil was triturated with about 30 ml of a 3:1 isopropyl ether/ethyl acetate mixture at room temperature
  8. filtrationFiltration

Sources & evidence

ORD record
ord-517fbb719d2d444e85cb9e8c0944ad6c
Source dataset
uspto-grants-1976_05
Patent number
US03956500

Reaction notes

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