Phosgene → HCID 12151506, compound

HRID 479876Notes

Reaction equation

HRID 479876 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][O:6][C:7](=[O:11])[C:8]([CH3:10])=[CH2:9].[C:12](Cl)([Cl:14])=[O:13]>C(Cl)Cl>[CH3:2][N:3]([CH2:4][CH2:5][O:6][C:7](=[O:11])[C:8]([CH3:10])=[CH2:9])[C:12]([Cl:14])=[O:13]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 22475658HCID 22475658, compound

Product 1

HCID 12151506HCID 12151506, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

N-Methyl-N-(2-methacryloyloxyethyl)amine hydrochloride (95.0 g, 0.529 mol) produced in Example 1 was suspended in methylene chloride (300 ml) and heated to 50° C. Phosgene (7.85 g, 0.793 mol) was introduced into the resultant suspension over two hours. The resultant reaction mixture was further stirred for one hour, and then the methylene chloride was removed from the mixture to produce N-methyl-N-(2-methacryloyloxyethyl)carbamoyl chloride (106.6 g, almost quantitative yield, purity: 98%) as a colorless transparent liquid. The product was analyzed through gas chromatography (column: silicone SE-30 20% glass column (2 m), injection temperature: 220° C., detection temperature: 230° C.). FIGS. 3 and 4 show the infrared spectrum and NMR spectrum of the product, respectively.

Workup

  1. customThe resultant reaction mixture
  2. customthe methylene chloride was removed from the mixture

Sources & evidence

ORD record
ord-127672a56e5f4f6dae5f858ba2c96500
Source dataset
uspto-grants-2003_11
Patent number
US06646156B2

Reaction notes

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