Hydrochloric Acid → HCID 20330155, compound

HRID 2057767Notes

Reaction equation

HRID 2057767 reaction equation
[C:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([N+:18]([O-:20])=[O:19])=[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:14]=2[CH:27]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B#B.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([N+:18]([O-:20])=[O:19])=[C:15]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:14]=2[CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 6328200DiboronHCID 20330184HCID 20330184, compound

Product 1

HCID 20330155HCID 20330155, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product of Step A is dissolved in 50 ml. of tetrahydrofuran and treated with 5 ml. of 1 N diborane in tetrahydrofuran at about 20° C. over a period of about 16 hours. The mixture is treated with 5 ml. of 6 N hydrochloric acid and heated on a steam bath for about 1/2 hour. 20 ml. of saturated sodium bicarbonate solution is added, the mixture is extracted with chloroform and the extracts are dried, then evaporated to provide a residue. The residue is recrystallized from a mixture of isopropanol and water to yield red needles of 5-benzylamino-2-nitro-3-phenylbenzofuran, m.p. 118°-120° C. having the structure ##STR12##

Workup

  1. additionThe mixture is treated with 5 ml
  2. extractionthe mixture is extracted with chloroform
  3. customthe extracts are dried
  4. customevaporated
  5. customto provide a residue
  6. customThe residue is recrystallized from a mixture of isopropanol and water

Sources & evidence

ORD record
ord-1dabfd31e1ce40c48d10fc7623cd367d
Source dataset
uspto-grants-1980_07
Patent number
US04212865

Reaction notes

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