m-Chloroperbenzoic acid → HCID 14657015, compound

HRID 1494516Notes

Reaction equation

HRID 1494516 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[NH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[C@@H:22]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:24]([OH:25])[CH2:23]2)=[C:15]([S:30][NH2:31])[N:14]=1>C(O)C>[NH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[C@@H:22]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:24]([OH:25])[CH2:23]2)=[C:15]([S:30]([NH2:31])=[O:6])[N:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14657011HCID 14657011, compound

Product 1

HCID 14657015HCID 14657015, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of m-chloroperoxybenzoic acid (0.50 g, 2.5 mmol) in ethanol (50 mL) was added dropwise to an ice-cooled (0°-5° C.), stirred solution of 45 (0.75 g, 2.5 mmol) in ethanol (150 mL), during 15 min. The reaction mixture was allowed to stand at room temperature overnight and the crystalline product that deposited was collected by filtration. The product was washed with ethanol (2×15 mL) and air-dried to yield 0.24 g (31%) of 46. mp 178° C. (dec.). IR (KBr): 1040, 1300 (s, S=O), 3100-3600 (NH2, OH)cm-1 ; UV: λmax (pH 1) 329 nm (ε 3,800): λmax (pH 7) 323 nm (ε 5,800): λmax (pH 11) 323 nm (ε 3,700): 1H NMR (DMSO-d6): δ 6.27 (dd, 1, J=5.5 Hz, C1'H), 6.50 (s, 2, SONH2, exchanged with D2O), 6.94 (s, 2, NH2, exchanged with D2O), 8.43 (s, 1, C8H), and other sugar protons. Anal. Calcd. for C10H14N6O4S (314.32): C, 38.21; H, 4.49; N, 26.74; S, 10.20. Found: C, 38.34; H, 4.59; N, 26.47; S, 10.17.

Workup

  1. temperaturecooled (0°-5° C.)
  2. waitto stand at room temperature overnight
  3. filtrationthe crystalline product that deposited was collected by filtration
  4. washThe product was washed with ethanol (2×15 mL)
  5. customair-dried

Sources & evidence

ORD record
ord-6881a5e036f54fedb24096496eb39c7b
Source dataset
uspto-grants-1991_06
Patent number
US05026836

Reaction notes

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