Ethyl Acetate → HCID 18696597, compound

HRID 1870550Notes

Reaction equation

HRID 1870550 reaction equation
Cl[C:2]([Cl:12])(OC(=O)OC(Cl)(Cl)Cl)Cl.CO[C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[C:22]2[NH:25][C:26]([NH:28][N:29](C)C)=[O:27])=[CH:17][CH:16]=1.[C:32](=[O:35])(O)[O-].[Na+].[C:37](OCC)(=O)C>>[Cl:12][C:2]1[N:25]([C:22]2[C:23]3[C:18](=[CH:17][CH:16]=[C:15]([O:35][CH3:32])[CH:24]=3)[CH:19]=[CH:20][CH:21]=2)[C:26](=[O:27])[N:28]([CH3:37])[N:29]=1

Participants

5

Reactant 4

HCID 8857Ethyl Acetate2×HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 18696611HCID 18696611, compound

Product 1

HCID 18696597HCID 18696597, compound

Procedure

A solution of triphosgene (16.7 g) in ethyl acetate (130 mL) was heated to reflux and a suspension of the title compound of Step D (4.9 g) in ethyl acetate was added via cannula and the aid of a mechanical pump over a period of 40 min. The temperature was held at approximately 75° C. during the addition. After the addition was complete, the reaction mixture was heated at reflux for 2 h, cooled to room temperature and stirred overnight at room temperature. The reaction mixture was poured into a solution of saturated aqueous sodium bicarbonate, extracted with ethyl acetate, and the combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure to afford 4.9 g of the title compound of Step E as a white solid melting at 142-143° C. 1H NMR (CDCl3): δ 7.93 (dd,1H), 7.84 (d,1H), 7.43 (m,2H), 7.24 (dd,1H), 6.75 (d,1H), 3.87 (s,3H), 3.62 (s,3H).

Workup

  1. temperatureto reflux
  2. additionwas added via cannula
  3. additionThe temperature was held at approximately 75° C. during the addition
  4. additionAfter the addition
  5. temperaturethe reaction mixture was heated
  6. temperatureat reflux for 2 h
  7. extractionextracted with ethyl acetate
  8. dry with materialthe combined organic extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40232a28b4b440a293bfbc706d73444e
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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