2-Naphthalenesulfonyl chloride → HCID 86598199, compound

HRID 538082Notes

Reaction equation

HRID 538082 reaction equation
Cl.[N:2]1([C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[S:30](Cl)(=[O:32])=[O:31].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[S:30]([N:5]1[CH2:6][CH2:7][CH2:8][N:2]([C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=2)[CH2:3][CH2:4]1)(=[O:31])=[O:32]

Participants

5

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86598200HCID 86598200, compound

Product 1

HCID 86598199HCID 86598199, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(hexahydro-1H-1,4-diazepin-1-yl)-benzoic acid, ethyl ester hydrochloride (1:2) (0.01 mol) and 2-naphthalenesulfonyl chloride (0.011 mol) in DCM p.a. (150 ml) was stirred at room temperature. NaHCO3 (saturated aqueous solution, 50 ml) was added and the reaction mixture was stirred for 4 hours at room temperature. The layers were separated. The organic layer was dried, filtered and the solvent evaporated. The residue was triturated under 2-propanol, filtered off and dried, yielding 4.5 g (quantitative yield) of 4-[hexahydro-4-(2-naphthalenylsulfonyl)-1H-1,4-diazepin-1-yl]-benzoic acid, ethyl ester (interm. 1).

Workup

  1. stirringthe reaction mixture was stirred for 4 hours at room temperature
  2. customThe layers were separated
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe residue was triturated under 2-propanol
  7. filtrationfiltered off
  8. customdried

Sources & evidence

ORD record
ord-506c1d53e2444af58129e7acc302a252
Source dataset
uspto-grants-2014_10
Patent number
US08865720B2

Reaction notes

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