Ethylenediamine → HCID 57732439, compound

HRID 1365069Notes

Reaction equation

HRID 1365069 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH:4]=O.[CH2:11]([NH2:14])[CH2:12][NH2:13]>O>[Br:10][C:7]1[CH:8]=[CH:9][C:2]2[NH:14][CH2:11][CH2:12][N:13]=[CH:4][C:3]=2[CH:6]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 57732439HCID 57732439, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A 5 mL microwave tube was charged with 2-fluoro-5-bromobenzaldehyde (1 g) and ethylenediamine (3 mL). The mixture was heated to 140° C. for 300 s using microwave irradiation. The reaction was diluted with water and extracted with diethyl ether. The organics were extracted with 1N HCl, and the pH of the aqueous layer was adjusted to ˜8 with 2.5M NaOH. The basic water layer was extracted again with diethyl ether. The organics were dried over magnesium sulfate, filtered and concentrated to dryness. Reconcentration from diethyl ether afforded 7-bromo-2,3-dihydro-1H-1,4-benzodiazepine as a yellow crystalline solid. H1 NMR (d6-dmso): 8.04 (s, 1H), 7.46 (d, 1H), 7.19 (dd, 1H), 7.07 (br t, 1H), 6.64 (d, 1H), 3.82 (m, 2H), 3.17 (m, 2H). Mass (ES+)=225.0 (100%).

Workup

  1. custommicrowave irradiation
  2. extractionextracted with diethyl ether
  3. extractionThe organics were extracted with 1N HCl
  4. extractionThe basic water layer was extracted again with diethyl ether
  5. dry with materialThe organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ffe38f5e1ddf4e23b70707c1db4e9bdf
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

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