Ethyl chloroformate → 2-Oxo-1,4-dihydro-2H-benzo[d][1,3]oxazine-6-carbonitrile

HRID 1991424Notes

Reaction equation

HRID 1991424 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][OH:11].CCN(C(C)C)C(C)C.Cl[C:22](OCC)=[O:23]>C1COCC1>[O:23]=[C:22]1[NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[CH2:10][O:11]1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 234604924-Amino-3-(hydroxymethyl)benzonitrile

Product 1

HCID 686891322-Oxo-1,4-dihydro-2H-benzo[d][1,3]oxazine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

20 mmol of 4-Amino-3-hydroxymethyl-benzonitrile were dissolved in THF. 1.2 eq. of DIPEA were added and the reaction cooled to 0° C. 3.5 eq of ethyl chloroformate were added dropwise and the reaction warmed to rt and stirred for another 15 min. The crude material was extracted form etyhlacetate and sat. NaHCO3. After separation, and drying of the organic layer the solvent was evaporated and the crude taken up in toluene. 2.5 ml of DBU were added and the reaction mixture refluxed for 4 h. The organic layer was extracted with water and the organic layer separated and reduced resulting in a yellow oil. Crude material was not further characterized.

Workup

  1. temperaturethe reaction warmed to rt
  2. extractionThe crude material was extracted form etyhlacetate and sat. NaHCO3
  3. customAfter separation
  4. customdrying of the organic layer the solvent
  5. customwas evaporated
  6. addition2.5 ml of DBU were added
  7. temperaturethe reaction mixture refluxed for 4 h
  8. extractionThe organic layer was extracted with water
  9. customthe organic layer separated
  10. customreduced resulting in a yellow oil

Sources & evidence

ORD record
ord-5d16c5472f1e471abcea8b4d85ec3299
Source dataset
uspto-grants-2010_01
Patent number
US07645776B2

Reaction notes

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