Methyl chloroformate → HCID 18961693, compound

HRID 1707569Notes

Reaction equation

HRID 1707569 reaction equation
[NH2:1][C:2]1[C:3]([F:15])=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH:11]([CH3:13])[CH3:12])[C:6]=2[CH:14]=1.C(N(CC)C1C=CC=CC=1)C.Cl[C:28]([O:30][CH3:31])=[O:29]>ClCCCl>[F:15][C:3]1[C:2]([NH:1][C:28]([O:30][CH3:31])=[O:29])=[CH:14][C:6]2[N:7]([CH:11]([CH3:13])[CH3:12])[C:8](=[O:10])[S:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 7061N,N-DiethylanilineHCID 13960994HCID 13960994, compound

Product 1

HCID 18961693HCID 18961693, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 5-amino-6-fluoro-3-isopropyl-2(3H)-benzothiazolone (2.1 g), N,N-diethyianiline (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 6-fluoro-5-methoxycarbonylamino -3-isopropyl-2(3H)-benzothiazolone (2.1 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-86721b94ec5544519d917bddddf0fb90
Source dataset
uspto-grants-1994_10
Patent number
US05354730

Reaction notes

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