Oxygen → HCID 53937847, compound

HRID 1585385Notes

Reaction equation

HRID 1585385 reaction equation
C(S[CH:4]=[CH2:5])=C.CN([C:9]1[CH:10]=[CH:11][C:12]2N=C3C(=CC(C=C3)=[N+](C)C)SC=2[CH:14]=1)C.[O:26]=[O:27].[CH2:28]1[C:33](=O)N(Cl)[C:30](=[O:31])[CH2:29]1.[F:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:38]=1[OH:44].[CH3:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]>C(Cl)Cl.C(OCC)(=O)C>[F:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:38]=1[O:44][C:47]1([C:46]2[CH:33]=[CH:28][CH:29]=[C:30]([OH:31])[CH:45]=2)[C:48]2([CH:11]3[CH2:10][CH:9]4[CH2:14][CH:4]([CH2:5][CH:49]2[CH2:50]4)[CH2:12]3)[O:27][O:26]1

Participants

9

Reactant 6

HCID 977OxygenHCID 4139Methylene blue cationHCID 8058HexaneHCID 12321Divinyl sulfideHCID 31398ChlorosuccinimideHCID 943922,6-Difluorophenol

Product 1

HCID 53937847HCID 53937847, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

The vinyl sulfide of Example 2(b) (0.100 g) was irradiated for 10 min in 20 mL of CH2Cl2 containing 2 mg of methylene blue with continuous oxygen bubbling at -40° C. using a 1000 W Na lamp. NCS (44.7 mg, 1 eq.) was added followed after 15 min by 100 mg (2.3 eq.) of 2,6-difluorophenol in 3 mL of CH2Cl2. The solution was allowed to warm to room temperature. After an hour, TLC showed a new material which emitted blue-green light when the plate was heated. The solution was evaporated, redissolved in a small amount of CH2Cl2 and the product isolated by two successive preparative TLC purifications first using 5-20% ethyl acetate in hexane and then using CH2Cl2 on a second plate yielding 11.2 mg of the product as a slightly yellow oil; 1H NMR (CDCl3) δ1.29-2.24 (m, 13H), 3.31 (br s, 1H), 5.00 (m, 1H), 6.68-7.6 (m, 7H).

Workup

  1. waitAfter an hour
  2. temperaturewas heated
  3. customThe solution was evaporated
  4. dissolutionredissolved in a small amount of CH2Cl2
  5. customthe product isolated by two successive preparative TLC purifications

Sources & evidence

ORD record
ord-88ab7825d56643fd9a6a176d528e2ed2
Source dataset
uspto-grants-1999_08
Patent number
US05936101

Reaction notes

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