Hydrochloric Acid → 2,3-Dihydro-6-iodo-3-propyl-2-thioxo-4(1H)-quinazolinone

HRID 1276621Notes

Reaction equation

HRID 1276621 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH3:9])=[O:5].[C:15](=S)=[S:16].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[I:14][C:11]1[CH:10]=[C:3]2[C:2](=[CH:13][CH:12]=1)[NH:1][C:15](=[S:16])[N:6]([CH2:7][CH2:8][CH3:9])[C:4]2=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 11430Potassium CarbonateHCID 221165242-Amino-5-iodo-N-propylbenzamide

Product 1

HCID 108933552,3-Dihydro-6-iodo-3-propyl-2-thioxo-4(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-5-iodo-N-propylbenzamide (1.0 g, 3.1 mmol) and carbon disulfide (0.59 g, 9.38 mmol) in dimethylformamide (3.1 mL) was added potassium carbonate (0.43g, 3.1 mmol). The reaction mixture was heated to reflux for 2 h, cooled to room temperature, and added dropwise to 1N hydrochloric acid (25 mL). The resulting precipitate was filtered, washed with water (2×10 mL), methanol (2×10 mL) and diethyl ether (10 mL), and dried to deliver 1.04 g of the title compound, m.p. 267-269° C.; 1H NMR (300 MHz, Me2SO-d6): δ0.90 (t,3H); 1.68 (m,2H); 4.33 (t,2H); 7.18 (d,1H); 8.04 (dd,1H); 8.19 (d, 1H); 12.98 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water (2×10 mL), methanol (2×10 mL) and diethyl ether (10 mL)
  5. customdried

Sources & evidence

ORD record
ord-9755d881cd6f42889fb7359daa78b093
Source dataset
uspto-grants-2000_12
Patent number
US06166208

Reaction notes

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