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

HRID 1276617Notes

Reaction equation

HRID 1276617 reaction equation
[C:1](=[S:3])=S.[OH-].[K+].[CH2:6]([NH2:9])[CH2:7][CH3:8].ClC(OCC)=O.[I:16][C:17]1[CH:25]=[C:21]([C:22]([OH:24])=O)[C:20]([NH2:26])=[CH:19][CH:18]=1.Cl>O>[I:16][C:17]1[CH:25]=[C:21]2[C:20](=[CH:19][CH:18]=1)[NH:26][C:1](=[S:3])[N:9]([CH2:6][CH2:7][CH3:8])[C:22]2=[O:24]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 7852PropylamineHCID 10928Ethyl chloroformateHCID 14797Potassium Hydroxide2×HCID 72911Benzoic acid, 2-amino-5-iodo-

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Carbon disulfide (16.4 mL, 0.28 mole) was added to a solution of potassium hydroxide (18.4 g, 0.28 mol) in water (100 mL). The reaction mixture was then cooled to 1 1° C. and n-propylamine (16.6 g, 0.28 mol) was added. An exotherm to 14° C. was observed and the reaction mixture became an orange slurry. The mixture was heated at 60° C. for 1 h and then cooled to 17° C. Ethyl chloroformate (32 g, 0.30 mole) was then added over a 30 min period allowing the temperature to rise to 25° C. Additional potassium hydroxide (9.2 g, 0.14 mol) was then added. After stirring for 20 min, 5-iodoanthranilic acid (26.4 g, 0.10 mol) was added and the resulting tan slurry was heated to 75° C. After 4.5 h, the reaction mixture was cooled to room temperature. Concentrated aqueous HCl was added to reduce the pH from 10 to 2. The aqueous phase was decanted from the oily solids, and the solids were washed two times with water (100 mL each). Methanol (100 mL) was added to crystallize the produce. The solids were recovered by filtration, washed with methanol (2 times with 15 mL), and dried. The 2,3-dihydro-6-iodo-3-propyl-2-thioxo-4(1H)-quinazolinone weighed 27.8 g and had a melting point of 267-269° C.

Workup

  1. additionwas added
  2. customto 14° C.
  3. temperaturecooled to 17° C
  4. customto rise to 25° C
  5. temperaturethe resulting tan slurry was heated to 75° C
  6. waitAfter 4.5 h
  7. temperaturethe reaction mixture was cooled to room temperature
  8. customThe aqueous phase was decanted from the oily solids
  9. washthe solids were washed two times with water (100 mL each)
  10. additionMethanol (100 mL) was added
  11. customto crystallize the produce
  12. filtrationThe solids were recovered by filtration
  13. washwashed with methanol (2 times with 15 mL)
  14. customdried

Sources & evidence

ORD record
ord-2b17d2b9333f4d6d845805368513b9b9
Source dataset
uspto-grants-2000_12
Patent number
US06166208

Reaction notes

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