Triethylamine → HCID 15425910, compound

HRID 551786Notes

Reaction equation

HRID 551786 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)=[O:20]>O1CCCC1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C:19]([O:21][C:22]2[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=2)=[O:20])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 5850963,4-Dihydro-2H-1,4-benzoxazine

Product 1

HCID 15425910HCID 15425910, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g of 3,4-dihydro-2H-1,4-benzoxazine, 1.03 ml of triethylamine, 27 ml of tetrahydrofuran and then 1.5 g of para-nitrophenyl chloroformate are introduced into a 100 ml round-bottomed flask. The reaction mixture is stirred at ambient temperature for three hours and then filtered. The solvent is evaporated under reduced pressure and the residue is taken up in dichloromethane and washed with a 2N aqueous hydrochloric acid solution and then twice with water. The organic phase is dried over magnesium sulfate and the solvent is evaporated under reduced pressure to result in 2.1 g of 4-nitrophenyl 2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate.

Workup

  1. filtrationfiltered
  2. customThe solvent is evaporated under reduced pressure
  3. washwashed with a 2N aqueous hydrochloric acid solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customto result in 2.1 g of 4-nitrophenyl 2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate

Sources & evidence

ORD record
ord-3c8824e9d51e44209426f77c3ebb2be4
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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