Methanol → methyl 3-isocyanatopropanoate

HRID 720214Notes

Reaction equation

HRID 720214 reaction equation
S(O)(O)(=O)=O.[CH3:6][O:7][C:8](=[O:12])[CH2:9][CH2:10][NH2:11].CO.C(N(CC)CC)C.[CH2:22]([O:24]C(Cl)=O)C>C(OCC)(=O)C.C(=S)=S>[CH3:6][O:7][C:8]([CH2:9][CH2:10][N:11]=[C:22]=[O:24])=[O:12]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 21889522HCID 21889522, compound

Product 1

HCID 2769480methyl 3-isocyanatopropanoateYield 89.3%

Reagents, catalysts & solvents 2

HCID 6348Carbon DisulfideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing 603.6 g of β-alanine-methylester sulfate and 1.5 liter of methyl alcohol, 1,256 ml of triethylamine was added at a freezing point and thereto, 235 ml of carbon disulfide was added dropwise at 10° C. or less. After the dropwise addition, the solution was stirred at 10° C. or less for 1 hour and then 288 ml of ethylchloroformate was added dropwise and in this state, the solution was stirred for 2 hours. After the reaction, the reaction solution was subjected to liquid separation with ethyl acetate and water. The extracted ethyl acetate layer was dried over magnesium sulfate and filtered and then the ethyl acetate was removed by distillation under reduced pressure to 389.1 g (yield: 89.3%) of the objective compound as an oily product.

Workup

  1. additionwas added at a freezing point
  2. additionAfter the dropwise addition
  3. stirringthe solution was stirred for 2 hours
  4. customAfter the reaction
  5. customthe reaction solution was subjected to liquid separation with ethyl acetate and water
  6. dry with materialThe extracted ethyl acetate layer was dried over magnesium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-6ecbaed300d749deb642809dba1c87a4
Source dataset
uspto-grants-2006_11
Patent number
US07135275B2

Reaction notes

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