Tetrahydrofuran → HCID 19967451, compound

HRID 976645Notes

Reaction equation

HRID 976645 reaction equation
[CH2:1]([O:8][NH:9][CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[CH3:20][N:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:22](Cl)=[O:23]>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[CH2:1]([O:8][N:9]([CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:22]([N:21]([CH3:20])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 15366668HCID 15366668, compound

Product 1

HCID 19967451HCID 19967451, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
130 °C

Procedure

A tube was charged with a stir bar, N-benzyloxy-N-(1-ethylpropyl)amine (2.0 g, 10.3 mmole), tetrahydrofuran (5 mL), triethylamine (4.31 mL), N-methyl-N-phenylcarbamoyl chloride (1.75 g, 10.3 mmole), and 4-dimethylaminopyridine (1 mg). The tube was flushed with nitrogen, sealed and then heated to 130° C. After 48 hours the reaction mixture was cooled to ambient temperature and concentrated under vacuum. The residue was purified by chromatography (silica gel; 9:1 hexanes:ethyl acetate) to provide 2.0 g of 1-benzyloxy-1-(1-ethylpropyl)-3-methyl-3-phenylurea.

Workup

  1. additionA tube was charged with a stir bar
  2. customThe tube was flushed with nitrogen
  3. customsealed
  4. temperatureAfter 48 hours the reaction mixture was cooled to ambient temperature
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by chromatography (silica gel; 9:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-f0f4904d40c049ad9a2e07137a9fa364
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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