m-Chloroperbenzoic acid → HCID 14503119, compound

HRID 1494515Notes

Reaction equation

HRID 1494515 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:28][C@H:27]([CH3:29])[C@@H:25]([OH:26])[C@H:23]2[OH:24])=[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:28][C@H:27]([CH3:29])[C@@H:25]([OH:26])[C@H:23]2[OH:24])=[C:15]([S:30]([NH2:31])=[O:6])[N:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14503116HCID 14503116, compound

Product 1

HCID 14503119HCID 14503119, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of m-chloroperoxybenzoic acid (0.10 g, 0.5 mmol) in ethanol (10 mL) was added dropwise to an ice-cooled stirred solution of 41 (0.15 g, 0.5 mmol) in ethanol (25 mL), during 15 min. The reaction mixture was allowed to stand at 0° C. overnight and then evaporated to dryness under reduced pressure. The residue was triturated with a mixture of ethanol (2 mL) and ethyl ether (30 mL). The precipitated crystalline product was collected by filtration and dried at 80° C. for 3 h to yield 70 mg (45%) of the title compound, mp >100° C. (dec.). IR (KBr): 1050 (vs, s, S=O), 3100-3600 (NH2, OH)cm-1 :UV: λmax (pH 1) 330 nm (ε 3,600): λmax (pH 7) 324 nm (4,400): λmax (pH 11) 321 nm 4,300): 1H NMR (DMSO-d6): δ 1.30 (d, 3, CH3), 5.80 (d, 1, J 5.25 Hz, C1'H), 6.51 (s, 2, SONH2, exchanged with D2O), 6.98 (s, 2, NH2, exchanged with D2O), 8.40 (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, 37.98; H, 4.41; N, 26.51; S, 9.91.

Workup

  1. temperaturecooled
  2. waitto stand at 0° C. overnight
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was triturated with a mixture of ethanol (2 mL) and ethyl ether (30 mL)
  5. filtrationThe precipitated crystalline product was collected by filtration
  6. customdried at 80° C. for 3 h

Sources & evidence

ORD record
ord-c0a453912ab84105b5fea0c3c1fb1b9f
Source dataset
uspto-grants-1991_06
Patent number
US05026836

Reaction notes

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