Hydrochloric Acid → HCID 135494524, compound

HRID 858243Notes

Reaction equation

HRID 858243 reaction equation
N12CCCN=C1CCCCC2.[Br:12][CH:13]([C:16]1[C:24]2[O:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)=[N:21][C:20]=2[CH:19]=[C:18]([OH:32])[CH:17]=1)[CH2:14]Br.Cl>C(#N)C>[Br:12][C:13]([C:16]1[C:24]2[O:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)=[N:21][C:20]=2[CH:19]=[C:18]([OH:32])[CH:17]=1)=[CH2:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 135518305HCID 135518305, compound

Product 1

HCID 135494524HCID 135494524, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.25 g, 1.65 mmol) was added into a solution of 7-(1,2-dibromoethyl)-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol (0.4 g, 0.96 mmol) and acetonitrile (4 mL). The reaction mixture was stirred for 24 h, poured into cold (0° C.) HCl (1N, 10 mL) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (CH2Cl2/hexanes/isopropyl alcohol 15/5/1) gave a white solid (185 mg, 58% yield, m.p. 228–230° C.); MS m/e 332 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography (CH2Cl2/hexanes/isopropyl alcohol 15/5/1)

Sources & evidence

ORD record
ord-95579d45fd3f45aba62db72ffbc92d46
Source dataset
uspto-grants-2006_12
Patent number
US07148247B2

Reaction notes

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