Water → HCID 18677024, compound

HRID 1634024Notes

Reaction equation

HRID 1634024 reaction equation
[F:1]C1C=CC=C(N)C=1N.[C:10](OCC)(=O)[CH2:11][C:12]([CH3:14])=O.C1CC[N:27]2[C:22](=[N:23]C[CH2:25][CH2:26]2)CC1.[OH2:30].CC1C=C[C:35]([CH3:38])=[CH:36]C=1>>[F:1][C:10]1[CH:11]=[CH:12][C:14]2[N:23]([C:35]([CH3:38])=[CH2:36])[C:22](=[O:30])[NH:27][C:26]=2[CH:25]=1

Participants

6

Reactant 5

HCID 962WaterHCID 7809P-XyleneHCID 8868Ethyl AcetoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27828353-Fluorobenzene-1,2-diamine

Product 1

HCID 18677024HCID 18677024, compoundYield 8%

Procedure

A mixture of 3-fluorobenzenediamine (6.3 g, 50.0 mmol) and ethyl acetoacetate (6.50 g, 50.0 mmol) and DBU (0.76 g, 5.0 mmol) in p-xylene (50 mL) was heated to reflux for 2 h. Water formed during reaction was removed with a Dean-Stark trap. After cooling, the solvent was removed in vacuo. The residue was purified by flash chromatography (gradient, hexanes:EtOAc 4:1 to 1:1) to give 0.76 mg (8%) of 5-fluoro-1-isopropenyl-1,3-dihydro-benzoimidazol-2-one, 261 and 1.10 (11%) of 6-fluoro-1-isopropenyl-1,3-dihydro-benzoimidazol-2-one 262 as white solids.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. customwas removed with a Dean-Stark trap
  4. temperatureAfter cooling
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by flash chromatography (gradient, hexanes:EtOAc 4:1 to 1:1)

Sources & evidence

ORD record
ord-bb05a86b9f4c4232ba94bc7c835a6097
Source dataset
uspto-grants-2003_01
Patent number
US06506738B1

Reaction notes

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