3-chloro-2-[3-(3-chloro-propyl)-ureido]-benzoic Acid → 8-chloro-3,4-dihydro-2H-1-oxa-4a,9-diaza-anthracen-10-one

HRID 1059702Notes

Reaction equation

HRID 1059702 reaction equation
[Cl:1][C:2]1[C:3]([NH:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17]Cl)=[O:13])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6]>O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]2[C:3]=1[N:11]=[C:12]1[N:14]([CH2:15][CH2:16][CH2:17][O:13]1)[C:5]2=[O:6]

Participants

3

Reactant 1

HCID 185451933-chloro-2-[3-(3-chloro-propyl)-ureido]-benzoic Acid

Product 1

HCID 114590268-chloro-3,4-dihydro-2H-1-oxa-4a,9-diaza-anthracen-10-oneYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250 mL round bottom flask is charged with 3-chloro-2-[3-(3-chloro-propyl)-ureido]-benzoic acid (3.40 g, 11.7 mmol) and 50 mL of 10% aqueous KHCO3, and warmed to reflux for 1 hour. 50 mL of H2O is added and the solution is allowed to cool to room temperature, then to 0° C. The resulting yellow solid is collected by filtration to provide 2.32 g of crude product, which is recrystallized from CH2Cl2-isopropyl ether to provide the product as a white solid: 1.10 g (4.6 mmol, 40% yield). M.p. 206.7-207.9° C. 1H NMR (CDCl3): 8.09 (d, J 8, 1H), 7.77 (d, J=8, 1H), 7.24 (t, J=8, 1H), 4.54 (t, J=5, 2H), 4.14 (t, J=6, 2H), 2.32 (m, 2H). MS (CI): 237 (M+H, 100).

Workup

  1. temperaturewarmed
  2. temperatureto reflux for 1 hour
  3. customto 0° C
  4. filtrationThe resulting yellow solid is collected by filtration
  5. customto provide 2.32 g of crude product, which
  6. customis recrystallized from CH2Cl2-isopropyl ether

Sources & evidence

ORD record
ord-2f91d00170c84a688f22eb0c470ede16
Source dataset
uspto-grants-2003_02
Patent number
US06521630B1

Reaction notes

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