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2-Propenoic acid, 3,3-diethoxy-, ethyl ester → 4-Ethoxy-7,8-difluoro-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 900124
Notes
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Reaction equation

HRID 900124 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[NH2:10].[CH2:11]([O:13][C:14](=O)[CH:15]=[C:16](OCC)[O:17]CC)[CH3:12]>C(O)(=O)C>[CH2:11]([O:13][C:14]1[CH2:15][C:16](=[O:17])[NH:10][C:3]2[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=2[N:1]=1)[CH3:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 1693882-Propenoic acid, 3,3-diethoxy-, ethyl esterHCID 27367551,2-Diamino-4,5-difluorobenzene

Product 1

HCID 589579284-Ethoxy-7,8-difluoro-1,3-dihydro-benzo[b][1,4]diazepin-2-oneYield 80.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1,2-diamino-4,5-difluorobenzene (4.0 g, 27.75 mmol) in xylenes (50 mL) at 140° C. was added acetic acid (200 μL) followed by a solution of 3,3-diethoxyacrylic acid ethyl ester (5.22 g, 27.75 mmol) in xylenes (25 mL) over 1 hour. The reaction was heated at 140° C. for 2 hours, was cooled to room temperature, and was concentrated. The residue was triturated in hexanes to provide 5.38 g of 4-ethoxy-7,8-difluoro-1,3-dihydro-benzo[b][1,4]diazepin-2-one. 1H NMR (CDCl3) δ 7.05 (q, 1H), 6.87 (q, 1H), 4.29 (q, 2H), 3.18 (s, 2H), 1.35 (t, 3H).

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationwas concentrated
  3. customThe residue was triturated in hexanes

Sources & evidence

ORD record
ord-6c09ee09b5c94312bd77c08d2c464985
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07358242B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes