Benzoic acid, 2-amino-5-iodo- → 6-Iodo-2-trichloromethyl-1,2-dihydro-quinazolin-4-one

HRID 2257508Notes

Reaction equation

HRID 2257508 reaction equation
[I:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([NH2:11])=[CH:4][CH:3]=1.[Cl:12][C:13]([Cl:18])([Cl:17])[C:14](=[NH:16])[O-]>C(O)C>[I:1][C:2]1[CH:10]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:11][CH:14]([C:13]([Cl:18])([Cl:17])[Cl:12])[NH:16][C:7]2=[O:9]

Participants

4

Reactant 2

HCID 72911Benzoic acid, 2-amino-5-iodo-HCID 215840462,2,2-Trichloroethanimidate

Product 1

HCID 190749436-Iodo-2-trichloromethyl-1,2-dihydro-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 5-iodoanthranilic acid (131.5 g, 500 mmol) in ethanol (700 mL), 2,2,2-trichloroacetimidate (88.2 g, 500 mmol) was added. The reaction mixture was heated at 45° C. for 3 days under stirring. The solid formed was filtered and washed with fresh ethanol and air-dried. Yield 129.51 g (66.4%). Mp 224°-225° C. 'H-NMR (DMSO) 7.59 (d, 1 h, J=8.6 Hz), 8.21 (dd, 1H, J=2 Hz, J=7.5 Hz), 8.44, 1H, J=1.9 Hz), 13.55 (bs, 1H).

Workup

  1. customThe solid formed
  2. filtrationwas filtered
  3. washwashed with fresh ethanol
  4. customair-dried

Sources & evidence

ORD record
ord-f7a3cfa5d81a463a91b4032e6fcfbb16
Source dataset
uspto-grants-1997_08
Patent number
US05658902

Reaction notes

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