Triethylamine → HCID 21469077, compound

HRID 1938163Notes

Reaction equation

HRID 1938163 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:5].C(N(CC)CC)C.[C:25](=O)(OC(Cl)(Cl)Cl)[O:26]C(Cl)(Cl)Cl>ClCCl>[I:17][C:14]1[CH:13]=[C:3]2[C:2](=[CH:16][CH:15]=1)[NH:1][C:25](=[O:26])[N:6]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:4]2=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 21469060HCID 21469060, compound

Product 1

HCID 21469077HCID 21469077, compoundYield 237.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.6 g of 2-amino-5-iodo-N-(2-methoxycarbonylethyl)benzamide were introduced with 2.66 g (26.3 mmol) of triethylamine into 50 ml of dichloromethane and, under nitrogen, 1.21 g (4.1 mmol) of bis(trichloromethyl) carbonate dissolved in 15 ml of dichloromethane were added dropwise. The mixture was refluxed for 2 h and, after cooling, added to ice-water. The aqueous phase was extracted with dichloromethane, and the organic phase was dried and concentrated. 3.64 g (74%) of 6-iodo-3-(2-methoxycarbonylethyl)quinazoline-2,4-dione [RF 0.52 (ethyl acetate/n-heptane, 2:1)] were obtained as a yellowish solid.

Workup

  1. additionwere added dropwise
  2. temperatureThe mixture was refluxed for 2 h
  3. temperatureafter cooling
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. customthe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-35771659ff7a4dd582ddbd5ace5c53e1
Source dataset
uspto-grants-1997_12
Patent number
US05693637

Reaction notes

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