Hydrochloric Acid → HCID 20330143, compound

HRID 2057768Notes

Reaction equation

HRID 2057768 reaction equation
[N+:1]([C:4]1[O:5][C:6]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=O)[CH2:21][CH3:22])=[CH:15][C:7]=2[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O-:3])=[O:2].B#B.Cl>O1CCCC1>[N+:1]([C:4]1[O:5][C:6]2[CH:18]=[CH:17][C:16]([NH:19][CH2:20][CH2:21][CH3:22])=[CH:15][C:7]=2[C:8]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6328200DiboronHCID 20330177HCID 20330177, compound

Product 1

HCID 20330143HCID 20330143, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.8 g. of 2-nitro-3-phenyl-5-propionamidobenzofuran in 50 ml. of tetrahydrofuran is added 10 ml. of 1 N diborane, and the solution is stirred for about 18 hours under a nitrogen atmosphere. To this mixture is cautiously added 5 ml. of 6 N hydrochloric acid. The mixture is heated to its reflux temperature and maintained at reflux for about 30 minutes. The solution is evaporated to provide a residue which is partitioned between cold sodium bicarbonate solution and chloroform. The chloroform extracts are dried, then evaporated to provide a red residue which is recrystallized from aqueous ethanol to provide red crystals of 2-nitro-3-phenyl-5-(n-propyl)aminobenzofuran, m.p. 158°-160° C.

Workup

  1. temperatureThe mixture is heated to its
  2. temperaturereflux temperature
  3. temperaturemaintained
  4. temperatureat reflux for about 30 minutes
  5. customThe solution is evaporated
  6. customto provide a residue which
  7. customis partitioned between cold sodium bicarbonate solution and chloroform
  8. dry with materialThe chloroform extracts are dried
  9. customevaporated
  10. customto provide a red residue which
  11. customis recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-937ad10596974e30a8b7730e88fbdd54
Source dataset
uspto-grants-1980_07
Patent number
US04212865

Reaction notes

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