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Triphosgene → 3-Dibenzylamino-6,7-difluoro-1H-quinazoline-2,4-dione

HRID 729398
Notes
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Reaction equation

HRID 729398 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH:9][C:10](=[O:20])[C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[NH2:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:21]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[N:9]1[C:10](=[O:20])[C:11]2[C:12](=[CH:13][C:14]([F:18])=[C:15]([F:17])[CH:16]=2)[NH:19][C:29]1=[O:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 866071322-Amino4,5-difluorobenzoic acid, 2,2-dibenzylhydrazide

Product 1

HCID 219790003-Dibenzylamino-6,7-difluoro-1H-quinazoline-2,4-dioneYield 198.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

2-Amino-4,5-difluorobenzoic acid, 2,2-dibenzylhydrazide (Example 15) (0.81 g, 2.2 mmol) and triphosgene (0.33 g, 1.1 mmol) are combined in 100 mL of methylene chloride and stirred at 25° C. for 20 hours. The solution is poured into 200 mL of saturated NaHCO3, the layers are separated, and the aqueous layer is washed three times with ethyl acetate. The combined organic layers are dried over magnesium sulfate and then concentrated to give 0.86 g of the title compound as a solid. MS CI: m/z 394 (MH+).

Workup

  1. customthe layers are separated
  2. washthe aqueous layer is washed three times with ethyl acetate
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c89cc1e97cb646559a16e00824affd92
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07582627B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes