Ethyl Acetate → HCID 21841987, compound

HRID 1737212Notes

Reaction equation

HRID 1737212 reaction equation
Cl[C:2]([Cl:12])(OC(=O)OC(Cl)(Cl)Cl)Cl.C[N:14](C)[NH:15][C:16]([NH:18][C:19]1C(C)=[CH:27][CH:26]=[CH:25][C:20]=1[C:21](OC)=O)=[O:17].[C:31](=O)(O)[O-].[Na+].[C:36]([O:39][CH2:40]C)(=[O:38])[CH3:37]>>[Cl:12][C:2]1[N:18]([C:19]2[C:20]([CH3:21])=[CH:25][CH:26]=[CH:27][C:37]=2[C:36]([O:39][CH3:40])=[O:38])[C:16](=[O:17])[N:15]([CH3:31])[N:14]=1

Participants

5

Reactant 4

HCID 8857Ethyl Acetate2×HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 21841990HCID 21841990, compound

Product 1

HCID 21841987HCID 21841987, compound

Procedure

Into a solution of triphosgene (51.5 g, 174 mmol) in ethyl acetate (500 mL) heated to 75° C. was pumped a slurry of the title compound of Step B (15.57 g, 62 mmol) in ethyl acetate (100 mL) over 40 min. The mixture was held at 75° C. during the entire addition and then for an additional 2 h. The mixture was cooled to room temperature and stirred overnight. The reaction mixture was poured into saturated sodium bicarbonate solution and back-extracted with ethyl acetate. The combined organic phases were dried (MgSO4) and concentrated under reduced pressure to afford the title compound of Step C (14.59 g) as an off white solid. 1H NMR (CDCl3): δ 8.01 (dd,1H), 7.58 (d,1H), 7.50 (t,1H), 3.82 (s,3H), 3.56 (s,3H), 2.28 (s,3H).

Workup

  1. customover 40 min
  2. additionThe mixture was held at 75° C. during the entire addition
  3. extractionback-extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7549737707e4f8c8e4d77e0c8bce4b5
Source dataset
uspto-grants-1999_10
Patent number
US05962436

Reaction notes

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