Hydrazine hydrate (1:1) → 9-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid hydrazide

HRID 628063Notes

Reaction equation

HRID 628063 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]2[CH2:9][CH2:10][O:11][C:12]3[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:13]=3[C:14]=2[N:15]=1)=O)C.O.[NH2:22][NH2:23]>C(O)C>[Br:20][C:17]1[CH:18]=[CH:19][C:12]2[O:11][CH2:10][CH2:9][C:8]3[S:7][C:6]([C:4]([NH:22][NH2:23])=[O:3])=[N:15][C:14]=3[C:13]=2[CH:16]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67050521Ethyl 9-bromo-4,5-dihydrobenzo[2,3]oxepino[4,5-D]thiazole-2-carboxylate

Product 1

HCID 670967839-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid hydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Alternatively, to a suspension of 9-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid ethyl ester (4.55 g) in ethanol (50 mL) was added hydrazine monohydrate (5 mL) and the reaction heated at reflux for 16 h. After cooling to room temperature, the solid was filtered, washed with diethyl ether and air-dried to give 9-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid hydrazide.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 16 h
  3. filtrationthe solid was filtered
  4. washwashed with diethyl ether
  5. customair-dried

Sources & evidence

ORD record
ord-62e3716e001647bbad31f8a12305d775
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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