Tris(2-carboxyethyl)phosphine hydrochloride → 1,2,7-trimethyl-1H-benzimidazol-5-ylamine hydrochloride

HRID 1846439Notes

Reaction equation

HRID 1846439 reaction equation
[N:1]([C:4]1[CH:14]=[C:13]([CH3:15])[C:7]2[N:8]([CH3:12])[C:9]([CH3:11])=[N:10][C:6]=2[CH:5]=1)=[N+]=[N-].[ClH:16].C(CCP(CCC(O)=O)CCC(O)=O)(O)=O>O1CCOCC1>[ClH:16].[CH3:12][N:8]1[C:7]2[C:13]([CH3:15])=[CH:14][C:4]([NH2:1])=[CH:5][C:6]=2[N:10]=[C:9]1[CH3:11]

Participants

4

Reactant 2

HCID 2734570Tris(2-carboxyethyl)phosphine hydrochlorideHCID 866638995-azido-1,2,7-trimethyl-1H-benzimidazole

Product 1

HCID 669781471,2,7-trimethyl-1H-benzimidazol-5-ylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under a nitrogen atmosphere, 200 mg (1.00 mmol) 5-azido-1,2,7-trimethyl-1H-benzimidazole, 420 mg (1.50 mmol) tris(2-carboxyethyl)phosphine-hydrochloride, 1.5 mL dioxane and 0.5 mL E-water were combined and the mixture was stirred at RT overnight. Then the reaction mixture was acidified and extracted with EtOAc. The aqueous phase was made alkaline with aqueous sodium hydroxide solution and extracted with DCM. The organic phase was dried on sodium sulphate, filtered and evaporated down. The residue was combined with ethereal hydrochloric acid and the hydrochloride that settled out as precipitate was suction filtered and dried.

Workup

  1. extractionextracted with EtOAc
  2. extractionextracted with DCM
  3. customThe organic phase was dried on sodium sulphate
  4. filtrationfiltered
  5. customevaporated down
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-fdcbdc1e35564c5fb8ef3365c1af8bf2
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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