Hydrochloric Acid → HCID 13732639, compound

HRID 1731611Notes

Reaction equation

HRID 1731611 reaction equation
[CH2:1]([N:8]1[C:12](=O)[CH:11]2[CH2:14][C:15]3[C:16]([O:23][CH3:24])=[C:17]([O:21][CH3:22])[CH:18]=[CH:19][C:20]=3[CH:10]2[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:26].O>O1CCCC1>[ClH:26].[CH2:1]([N:8]1[CH2:12][CH:11]2[CH2:14][C:15]3[C:16]([O:23][CH3:24])=[C:17]([O:21][CH3:22])[CH:18]=[CH:19][C:20]=3[CH:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13732637HCID 13732637, compound

Product 1

HCID 13732639HCID 13732639, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6.19 g. of the resultant compound of Example 4 suspended in 15 ml. tetrahydrofuran (THF) was treated with 110 ml. 1M BH3 in THF under nitrogen atmosphere. The solution was refluxed 4 hours, then cooled and a solution of 35 ml. concentrated hydrochloric acid and 35 ml. water was added slowly. The solution was refluxed for 20 minutes and then concentrated in vacuum. The residue was made basic with potassium hydroxide solution and extracted with chloroform. The chloroform extracts were dried (K2CO3) and concentrated. The residue was acidified with HCl in isopropyl alochol and this solution was concentrated. Acetonitrile was added to give the product 5.78 g., m.p. 176°-178° C.

Workup

  1. temperatureThe solution was refluxed 4 hours
  2. temperaturecooled
  3. temperatureThe solution was refluxed for 20 minutes
  4. concentrationconcentrated in vacuum
  5. extractionextracted with chloroform
  6. dry with materialThe chloroform extracts were dried (K2CO3)
  7. concentrationconcentrated
  8. concentrationthis solution was concentrated
  9. additionAcetonitrile was added

Sources & evidence

ORD record
ord-5a8260e7bbe24c3b861124fe6d755008
Source dataset
uspto-grants-1986_11
Patent number
US04622405

Reaction notes

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