Hydrochloric Acid → HCID 54699044, compound

HRID 1497222Notes

Reaction equation

HRID 1497222 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])O[C:7](=[O:12])[C:6]=2[CH:13]=1.[C:14]([CH2:16]C(OCC)=O)#[N:15].C(N(CC)CC)C.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:13]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:10][C:9](=[O:11])[C:16]([C:14]#[N:15])=[C:7]2[OH:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 8471TriethylamineHCID 784805-Chloroisatoic anhydride

Product 1

HCID 54699044HCID 54699044, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-chloro-1,2-dihydro-4H-3,1-benzoxazine-2,4-dione (2 g, 10.1 mmol, Eq: 1.00), ethyl cyanoacetate (1.15 g, 1.08 ml, 10.1 mmol, Eq: 1.00) and triethylamine (14.5 g, 20.0 ml, 143 mmol, Eq: 14.2) in DMF (1.00 ml) was stirred at RT for 65 h. Then 1N HCl was added and the reaction mixture was extracted with ethyl acetate (3×). The combined extracts were washed brine. An off-white solid precipitated and was filtered off (337 mg). MS (ESI): 219.1 (M−H)−.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (3×)
  2. washThe combined extracts were washed brine
  3. customAn off-white solid precipitated
  4. filtrationwas filtered off (337 mg)

Sources & evidence

ORD record
ord-4d4da2fdc81c4be68c2070120cceff48
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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