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

HRID 392071Notes

Reaction equation

HRID 392071 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 20 (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 21).

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-0660cfe4e60944a6ab0bd5ebdb450292
Source dataset
uspto-grants-2004_10
Patent number
US06800628B2

Reaction notes

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