1-Decanethiol → HCID 85802880, compound

HRID 1671849Notes

Reaction equation

HRID 1671849 reaction equation
Cl[C:2]1[C:31](Cl)=[CH:30][C:29]2[C:4](=[N:5][C:6]3[C:7]4[C:16]([C:17]5[C:26]([C:27]=3[N:28]=2)=[N:25][C:24]2[C:19](=[CH:20][C:21](Cl)=[C:22](Cl)[CH:23]=2)[N:18]=5)=[N:15][C:14]2[C:9](=[CH:10][C:11](Cl)=[C:12](Cl)[CH:13]=2)[N:8]=4)[CH:3]=1.[CH2:37]([SH:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:37]([S:47][C:2]1[C:31]([S:47][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[CH:30][C:29]2[C:4](=[N:5][C:6]3[C:7]4[C:16]([C:17]5[C:26]([C:27]=3[N:28]=2)=[N:25][C:24]2[C:19](=[CH:20][C:21]([S:47][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[C:22]([S:47][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH:23]=2)[N:18]=5)=[N:15][C:14]2[C:9](=[CH:10][C:11]([S:47][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[C:12]([S:47][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH:13]=2)[N:8]=4)[CH:3]=1)[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

5

Reactant 3

HCID 89171-DecanethiolHCID 11430Potassium CarbonateHCID 59768779HCID 59768779, compound

Product 1

HCID 85802880HCID 85802880, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,3,8,9,14,15-hexachloro-5,6,11,12,17,18-hexaazatrinaphthylene (3.00 g, 5.08 mmol), 1-decanethiol (13.74 mL, 66.75 mmol) and K2CO3 (25.55 g, 185.00 mmol) in DMF (250 mL) was stirred at 80° C. for 72 hrs under nitrogen. After cooled down to room temperature, solvent was removed in vacuo. To the solid residue, water and dichloromethane was added. The organic layer was separated and the aqueous layer was extracted with dichloromethane (100 mL) twice. The combined organic layer was dried over magnesium sulfate and filtered. Solvent was evaporated under reduced pressure to give a yellow solid. The yellow solid was purified by flash chromatography on silica gel eluting with hexane:dichloromethane (1:1) to give a solid (4.00 g, 56% yield). The yellow product was washed with hot acetone in a Soxhlet extractor for 12 hrs before sending for elemental analysis. 1H (300 MHz, CD2Cl2) δ 7.49 (s, 6H), 2.81 (t, J=6.8 Hz, 12H), 1.55 (p, J=6.6 Hz, 12H), 1.50-1.25 (m, 84H), 0.93 (t, J=6.3 Hz, 18H). 13C NMR (75 MHz, CD2Cl2): 143.36, 141.84, 140.42, 122.26, 33.22, 32.36, 30.14, 30.07, 29.91, 29.82, 28.24, 23.13, 14.32. HRMS MALDI-TOF (with CHCA as matrix), 1417.8975; calcd. For C84H133N6S6 (M+H), 1417.8911. Anal. Calcd. For C84H132N6S6: C, 71.13; H, 9.38; N, 5.93. Found: C, 70.92; H, 9.38; N, 5.90.

Workup

  1. temperatureAfter cooled down to room temperature
  2. customsolvent was removed in vacuo
  3. additionTo the solid residue, water and dichloromethane was added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with dichloromethane (100 mL) twice
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customSolvent was evaporated under reduced pressure
  9. customto give a yellow solid
  10. customThe yellow solid was purified by flash chromatography on silica gel eluting with hexane:dichloromethane (1:1)

Sources & evidence

ORD record
ord-7be89732da4b48888c0f40c0184db95c
Source dataset
uspto-grants-2011_08
Patent number
US07994423B2

Reaction notes

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