Citric Acid → HCID 57901784, compound

HRID 1851429Notes

Reaction equation

HRID 1851429 reaction equation
Br[CH2:2][CH2:3][NH:4][C:5]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:16][S:17]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=[O:19])=[O:18])=[O:6].[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[O:6]1[CH2:2][CH2:3][N:4]=[C:5]1[C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:16][S:17]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 57901813HCID 57901813, compound

Product 1

HCID 57901784HCID 57901784, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-bromoethyl)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (0.35 g) in tetrahydrofuran (6 mL) was slowly added sodium hydride (60% in oil, 0.04 g) at 0° C., and the mixture was stirred at room temperature overnight. To the reaction mixture was added 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography and the title compound (0.20 g, yield 71%) was obtained as colorless crystals from a fraction eluted with ethyl acetate. The crystals were recrystallized from ethyl acetate-hexane. melting point>260° C. (decomposition).

Workup

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e0e131ed3de8455bbcd539a15f741e68
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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