Hydrochloric Acid → HCID 9928779, compound

HRID 1585221Notes

Reaction equation

HRID 1585221 reaction equation
Cl.[N:2]1[C:6]2[CH2:7][CH2:8][CH:9]([C:11]([OH:13])=O)[CH2:10][C:5]=2[NH:4][CH:3]=1.S(Cl)(Cl)=O.[OH:18][C:19]1[CH:20]=[C:21]([CH:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.CN(C)C=O>[OH:18][C:19]1[CH:20]=[C:21]([CH:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([C:11]([CH:9]3[CH2:8][CH2:7][C:6]4[N:2]=[CH:3][NH:4][C:5]=4[CH2:10]3)=[O:13])[CH2:26]2)[CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 110301834,5,6,7-Tetrahydro-1H-benzoimidazole-5-carboxylic acidHCID 212222863-(3-Hydroxyphenyl)indoline

Product 1

HCID 9928779HCID 9928779, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.99 g of hydrochloride (racemic form) of 4,5,6,7-tetrahydrobenzimidazole-5-carboxylic acid, 0.15 ml of dimethyl formamide and 20 ml of thionyl chloride was refluxed for three hours. The resultant reaction solution was distilled to dryness under a reduced pressure. The residue consequently formed was added to a solution of 2.07 g of (+)-3-(3-hydroxyphenyl)indoline in 75 ml of tetrahydrofuran. This reaction solution was stirred at room temperature for 12 hours, then weakly alkalinized by addition of the saturated aqueous sodium bicarbonate solution, and extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and then distilled. The residue was refined by silica gel column chromatography to obtain 2.00 g of 5-[{3-(3-hydroxyphenyl)indolin-1-ylcarbonyl}]-4,5,6,7-tetrahydrobenzimidazole (56.8%) as an epimer mixture.

Workup

  1. temperaturewas refluxed for three hours
  2. customThe resultant reaction solution
  3. distillationwas distilled to dryness under a reduced pressure
  4. customThe residue consequently formed
  5. extractionextracted with chloroform
  6. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  7. distillationdistilled

Sources & evidence

ORD record
ord-e4b70f7f761c4e15a786b0f60277fef0
Source dataset
uspto-grants-1999_08
Patent number
US05936098

Reaction notes

Loading…