3,4-dihydro-1H-quinazoline-2-thione → HCID 21090615, compound

HRID 350965Notes

Reaction equation

HRID 350965 reaction equation
C(O[C:4](=[O:16])[CH:5](Br)[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)C.[NH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][NH:19][C:18]1=[S:27]>C(O)C>[N+:12]([C:9]1[CH:8]=[CH:7][C:6]([CH:5]2[S:27][C:18]3=[N:17][C:26]4[C:21]([CH2:20][N:19]3[C:4]2=[O:16])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:11][CH:10]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 36448543,4-dihydro-1H-quinazoline-2-thioneHCID 10424182Ethyl alpha-bromo-4-nitrobenzeneacetate

Product 1

HCID 21090615HCID 21090615, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of bromo-(4-nitrophenyl)acetic acid ethyl ester (0.92 g, 3.2 mmol) in ethanol (15 ml) was added to a suspension of 3,4-dihydro-1H-quinazoline-2-thione (0.5 g, 3.0 mmol) in ethanol (10 ml) and the resulting mixture was heated at reflux for 3 h. A brown solid was filtered, washed with ethanol, and dried under reduced pressure to yield 0.86 g (88%) of a yellowish solid. 1H NMR (500 MHz, DMSO-D6) δ ppm 4.89 (m, 2H) 5.95 (s, 1H) 7.12 (d, J=7.63 Hz, 1H) 7.17 (t, J=7.48 Hz, 1H) 7.26 (m, 2H) 7.82 (d, J=8.85 Hz, 2H) 8.25 (d, J=8.85 Hz, 2H). MS (ESI) m/z 326 (MH+); HPLC (Column YMC Xterra OSD 4.6×33 mm S 7) rt 1.53 min; Purity (93%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 3 h
  3. filtrationA brown solid was filtered
  4. washwashed with ethanol
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-482c54dfe5054105a6596d750e2d3755
Source dataset
uspto-grants-2007_02
Patent number
US07183302B2

Reaction notes

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