Ethylenediaminetetraacetic Acid → HCID 22324074, compound

HRID 1767664Notes

Reaction equation

HRID 1767664 reaction equation
[Li][C:2]([CH3:5])([CH3:4])[CH3:3].Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.IC1C=C[C:17]([NH2:24])=[C:18]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:19]=1.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.[OH-].[Na+]>C1COCC1.[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:24][C:17]1[CH:4]=[C:2]([CH3:5])[C:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:19][C:18]=1[S:20]([NH2:23])(=[O:22])=[O:21]

Participants

9

Reactant 5

HCID 6049Ethylenediaminetetraacetic AcidHCID 79732-BromopyridineHCID 14798Sodium HydroxideHCID 223240882-Amino-5-iodobenzenesulfonamide2×HCID 178418306HCID 178418306, compound

Product 1

HCID 22324074HCID 22324074, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of t-BuLi (1.7 M in pentane, 25 ml, 42 mmol) in dry THF at −78° C. was added 2-bromopyridine (1.9 ml, 20 mmol) in such a rate that the temperature did not exceed −70° C. The mixture was stirred for another 30 min at −78° C. A solution of ZnCl2 (2M in THF, 30 ml, 60 mmol) was added slowly and the cooling bath was removed and warmed to 20° C. 5-Iodo-2-aminobenzenesulfonamide (see compound 37) (1.0 g, 3.2 mmol) and Pd(PPh3)4 (0.3 g, 8 mol %) was added and the mixture was refluxed for 6 h. The THF was evaporated and the residue was treated with EDTA (53 g, 0.18 mol) and made slightly basic (pH≈8–9) with 1 M NaOH followed by extraction with EtOAc (3×100 ml), drying (Na2SO4). The organic layer was concentrated to ca. 40 ml and n-hexane was added slowly. The product was filtered off, yielding 0.72 g (87%) of 2-amino-4-methyl-5-(2-pyridyl)-1-benzenesulfonamide as light-yellow crystals. The product was further transformed by Method G (using cyclohexanecarboxaldehyde). M.p. 229–231° C.

Workup

  1. customdid not exceed −70° C
  2. customthe cooling bath was removed
  3. temperaturewarmed to 20° C
  4. temperaturethe mixture was refluxed for 6 h
  5. customThe THF was evaporated
  6. extractionfollowed by extraction with EtOAc (3×100 ml)
  7. dry with materialdrying (Na2SO4)
  8. concentrationThe organic layer was concentrated to ca. 40 ml and n-hexane
  9. additionwas added slowly
  10. filtrationThe product was filtered off

Sources & evidence

ORD record
ord-c0b8304bc9db45ada6d4cc0e031687f8
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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