Dimethylcarbamoyl Chloride → HCID 13547276, compound

HRID 974007Notes

Reaction equation

HRID 974007 reaction equation
Cl.[CH2:2]([O:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:18][N:19]([CH3:23])[C:20](Cl)=[O:21]>C1COCC1.CN(C1C=CN=CC=1)C>[CH3:18][N:19]([CH3:23])[C:20]([NH:10][O:9][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:21]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 13547276HCID 13547276, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred slurry of benzyloxyamine hydrochloride (3.19 g, 20 mmol) in the THF (40 ml) at room temperature under nitrogen was added triethylamine (6.13 ml). This slurry was stirred, and dimethylcarbamyl chloride (1.84 ml) was added rapidly. 4-(N,N-dimethylamino)pyridine (1.0 g, 0.4 equiv.) was added, and the mixture was stirred for 20 hours. The mixture was filtered, and the filtrate evaporated. Purification by chromatography on silica provided N,N-dimethyl-N'benzyloxyurea as a colorless oil (1.62 g, 42% yield).

Workup

  1. stirringthe mixture was stirred for 20 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated
  4. customPurification by chromatography on silica

Sources & evidence

ORD record
ord-60075ae4cc6449d09e02d7bab8e2a324
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Reaction notes

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