Dimethylformamide dimethyl acetal → 9-Bromo-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-2-carboxylic acid 1-dimethylaminomethylideneamide

HRID 2044291Notes

Reaction equation

HRID 2044291 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[N:7]([N:8]=[C:9]([C:15]([NH2:17])=[O:16])[CH:10]=3)[C:6]=2[CH:18]=1.CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>O1CCOCC1>[CH3:21][N:22]([CH3:24])[CH:23]=[N:17][C:15]([C:9]1[CH:10]=[C:11]2[N:7]([N:8]=1)[C:6]1[CH:18]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:14][CH2:13][CH2:12]2)=[O:16]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 582043309-Bromo-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 582044179-Bromo-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-2-carboxylic acid 1-dimethylaminomethylideneamideYield 97.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 9-bromo-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-2-carboxylic acid amide (1.11 g, 3.60 mmol) and dimethylformamide dimethylacetal (1.44 mL, 10.8 mmol) in dry 1,4-dioxane (25 mL) was heated at 100° C. for 2 h, then concentrated in vacuo. The resultant residue was triturated in diethyl ether to give 9-Bromo-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-2-carboxylic acid 1-dimethylaminomethylideneamide as a yellow solid (1.27 g, 97%). LCMS: RT=3.27 min, M+H+=363/365.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-246d67ca2e3c4e8a8123954c627286b3
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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