Methyl chloroformate → HCID 19806966, compound

HRID 1681093Notes

Reaction equation

HRID 1681093 reaction equation
[NH2:1][C:2]1[C:10]2[CH:9]=[C:8]([CH3:11])[O:7][C:6]=2[C:5]([Cl:12])=[CH:4][C:3]=1[F:13].C(N(CC)C1C=CC=CC=1)C.[C:25](Cl)(=[O:28])[O:26][CH3:27]>O1CCCC1.C(OCC)(=O)C>[Cl:12][C:5]1[C:6]2[O:7][C:8]([CH3:11])=[CH:9][C:10]=2[C:2]([NH:1][C:25]([O:26][CH3:27])=[O:28])=[C:3]([F:13])[CH:4]=1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 7061N,N-DiethylanilineHCID 12040848HCID 12040848, compound

Product 1

HCID 19806966HCID 19806966, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-amino-7-chloro-5-fluoro-2-methylbenzo[b]furan (3.4 g) and N,N-diethylaniline (2.6 g) was dissolved in tetrahydrofuran (20 ml), and methyl chlorocarbonate (1.6 g) was dropwise added thereto at room temperature. The resultant mixture was heated under reflux for 3 hours. After cooling to room temperature, the reaction mixture was dissolved in ethyl acetate and washed with 10% hydrochloric acid. After removal of N,N-diethylaniline, the reaction mixture was dried and concentrated. The residue was washed with hexane to give 7-chloro-5-fluoro-4-methoxycarbonylamino-2-methylbenzo[b]furan (3.8 g; yield, 87%). m.p., 168°-169° C.

Workup

  1. customat room temperature
  2. temperatureunder reflux for 3 hours
  3. washwashed with 10% hydrochloric acid
  4. customAfter removal of N,N-diethylaniline
  5. customthe reaction mixture was dried
  6. concentrationconcentrated
  7. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-94f7fa8140714a51a19db53fa0f536c0
Source dataset
uspto-grants-1992_12
Patent number
US05169431

Reaction notes

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