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

HRID 988120Notes

Reaction equation

HRID 988120 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-ff966a3a804f429ebed496a7b2d2967f
Source dataset
uspto-grants-2003_10
Patent number
US06635643B2

Reaction notes

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