Dichloromethane → HCID 18696594, compound

HRID 1870542Notes

Reaction equation

HRID 1870542 reaction equation
Cl[C:2](Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C[N:14](C)[NH:15][C:16]([NH:18][C:19]1[C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:21][O:22][CH:23]=1)=[O:17].[CH2:29]([Cl:31])Cl>>[Cl:31][C:29]1[N:18]([C:19]2[C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:21][O:22][CH:23]=2)[C:16](=[O:17])[N:15]([CH3:2])[N:14]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 94429TriphosgeneHCID 18696604HCID 18696604, compound

Product 1

HCID 18696594HCID 18696594, compound

Procedure

Triphosgene (40.1 g) was added to a solution of crude title compound of Step C (15.4 g) in methylene chloride (550 mL) at 0° C. The mixture was heated at reflux for 4 h, cooled to room temperature and stirred overnight. The reaction mixture was concentrated to a brown oil which was dissolved in methylene chloride, washed with water and the aqueous layer extracted three times with methylene chloride. The combined organic extracts were dried (MgSO4), filtered and concentrated to a brown oil. Purification by flash chromatography (1:1 hexane:ethyl acetate) provided 5.34 g of the title compound of Step D as a yellow solid melting at 129-130° C. 1H NMR (CDCl3): δ 8.10 (d,1H), 7.72 (d,1H), 3.80 (s,3H), 3.52 (s,3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 h
  3. concentrationThe reaction mixture was concentrated to a brown oil which
  4. dissolutionwas dissolved in methylene chloride
  5. washwashed with water
  6. extractionthe aqueous layer extracted three times with methylene chloride
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to a brown oil
  10. customPurification by flash chromatography (1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-9ce5680b8f2a4df58b94c3b4e698825b
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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