m-Chloroperbenzoic acid → HCID 14503125, compound

HRID 1494509Notes

Reaction equation

HRID 1494509 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([S:11][NH2:12])[N:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:18]>CCO>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([S:11]([NH2:12])=[O:18])[N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14503124HCID 14503124, compound

Product 1

HCID 14503125HCID 14503125, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Aminopurine-6-sulfenamide 2 (182 mg, 1 mmol) was suspended in EtOH (100 mL) and cooled to 0° C. m-Chloroperoxybenzoic acid (85%, 200 mg, 1 mmol) was added portionwise during 1 h with stirring, and stirring continued for additional 30 min. After filtration, the filtrate was concentrated to half the volume in vacuo. Ethyl ether (50 mL) was added and allowed to stand in a refrigerator overnight. The precipitate was collected by filtration and washed with ether to obtain 115 mg (58%) of the desired compound, mp. >250° C., : UV λmax (pH 1) 332 nm (ε 4,600) 240 nm (sh): λmax (pH 7) 326 nm (ε 4,500): λmax (pH 11) 326 nm (ε 4,200), 283 nm (ε 2,800): IR(KBr): 1140 (SO) cm-1 : 1H NMR (DMSO-d6): δ 6.59 (br s, 2,--SONH2, exchangeable in D2O), 6.57 (br s, 2, NH2, exchangeable in D2O), 8.12 (s, 1, C8H), 12.50 (br s, 1, NH, exchangeable in D2O). Anal. Calcd for C5H6N6OS (198.21): C, 30.30: H, 3.05: N, 42.40: S, 16.18. Found: C, 30.02: H, 2.82: N, 42.64: S, 15.97.

Workup

  1. additionwas added portionwise during 1 h
  2. stirringstirring
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated to half the volume in vacuo
  5. additionEthyl ether (50 mL) was added
  6. customto stand in a refrigerator overnight
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with ether

Sources & evidence

ORD record
ord-481c71996fb645938b1798b2f3ddab40
Source dataset
uspto-grants-1991_06
Patent number
US05026836

Reaction notes

Loading…