Chlorosuccinimide → Methyl 7-(acetylamino)-6-chloro-1,3-benzodioxole-4-carboxylate

HRID 1879838Notes

Reaction equation

HRID 1879838 reaction equation
[C:1]([NH:4][C:5]1[C:10]2[O:11][CH2:12][O:13][C:9]=2[C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C1C(=O)N([Cl:25])C(=O)C1>C(#N)C>[C:1]([NH:4][C:5]1[C:10]2[O:11][CH2:12][O:13][C:9]=2[C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=1[Cl:25])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 22662748Methyl 7-(acetylamino)-1,3-benzodioxole-4-carboxylate

Product 1

HCID 22662759Methyl 7-(acetylamino)-6-chloro-1,3-benzodioxole-4-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of intermediate (2-c) (18.5 g) and NCS (11.4 g) in ACN (130 ml) was stirred and refluxed for one hour. The reaction mixture was cooled. The precipitate was filtered off, washed with ACN, with DIPE, then dried, yielding 18.2 g (87%) of methyl 7-(acetylamino)-6-chloro-1,3-benzodioxole-4-carboxylate (intermediate 2-d).

Workup

  1. temperaturerefluxed for one hour
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe precipitate was filtered off
  4. washwashed with ACN, with DIPE
  5. customdried

Sources & evidence

ORD record
ord-366113f64af647e9a3da4591d3f13bab
Source dataset
uspto-grants-2012_11
Patent number
US08318742B2

Reaction notes

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