Methyl chloroformate → HCID 19023224, compound

HRID 1034138Notes

Reaction equation

HRID 1034138 reaction equation
[NH2:1][C:2]1[C:3]([F:16])=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:12][C:13]#[CH:14])[C:6]=2[CH:15]=1.C(N(CC)C1C=CC=CC=1)C.Cl[C:29]([O:31][CH3:32])=[O:30]>ClCCCl>[F:16][C:3]1[C:2]([NH:1][C:29]([O:31][CH3:32])=[O:30])=[CH:15][C:6]2[N:7]([CH2:12][C:13]#[CH:14])[C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 7061N,N-DiethylanilineHCID 111603236‐Amino‐7‐fluoro‐4‐(prop‐2‐yn‐1‐yl)‐3,4‐dihydro‐2H‐ 1,4‐benzoxazin‐3‐one

Product 1

HCID 19023224HCID 19023224, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 6-amino-7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-one (2.1 g), N,N-diethylaniline (1.5 g) and methyl chloroformate (1.0 g) was dissolved in 1,2-dichloroethane (10 g), and the resultant mixture was heated under reflux for 3 hours. After cooling, the reaction mixture was washed with water, and the organic layer was concentrated. The residue was washed with methanol to give 7-fluoro-6-methoxycarbonylamino-4-propargyl-2H-1,4-benzoxazin-3(4H)-one (2.0 g).

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with water
  4. concentrationthe organic layer was concentrated
  5. washThe residue was washed with methanol

Sources & evidence

ORD record
ord-abf8d42ef2fc4b5ea63d9642c3c354a1
Source dataset
uspto-grants-1994_05
Patent number
US05314864

Reaction notes

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