Hydrochloric Acid → HCID 6857587, compound

HRID 71081Notes

Reaction equation

HRID 71081 reaction equation
C(C1C=CC(S[C:12]2[C:49]3[C:16](=[CH:17][C:18]4[C:19](C5C(C)=CC=CC=5C)(O)[C:20]5[C:45]([C:46](C6C(C)=CC=CC=6C)(O)[C:47]=4[CH:48]=3)=[CH:44][C:43]3[C:22](=[C:23](SC4C=CC(C(C)(C)C)=CC=4)[C:24]4[C:41]([C:42]=3SC3C=CC(C(C)(C)C)=CC=3)=[CH:40][C:39]3[C:38](C6C(C)=CC=CC=6C)(O)[C:37]6[C:28](=[CH:29][C:30]7[C:35]([CH:36]=6)=[C:34](SC6C=CC(C(C)(C)C)=CC=6)[C:33](SC6C=CC(C(C)(C)C)=CC=6)=[C:32](SC6C=CC(C(C)(C)C)=CC=6)[C:31]=7SC6C=CC(C(C)(C)C)=CC=6)[C:27](C6C(C)=CC=CC=6C)(O)[C:26]=3[CH:25]=4)[CH:21]=5)[C:15](SC3C=CC(C(C)(C)C)=CC=3)=[C:14](SC3C=CC(C(C)(C)C)=CC=3)[C:13]=2SC2C=CC(C(C)(C)C)=CC=2)=CC=1)(C)(C)C.Cl[Sn]Cl.Cl>O1CCOCC1>[CH:15]1[C:16]2[C:49](=[CH:48][C:47]3[C:18]([CH:17]=2)=[CH:19][C:20]2[C:45](=[CH:44][C:43]4[C:22]([CH:21]=2)=[CH:23][C:24]2[C:41](=[CH:40][C:39]5[C:26]([CH:25]=2)=[CH:27][C:28]2[C:37](=[CH:36][C:35]6[C:30]([CH:29]=2)=[CH:31][CH:32]=[CH:33][CH:34]=6)[CH:38]=5)[CH:42]=4)[CH:46]=3)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 86653931HCID 86653931, compound

Product 1

HCID 6857587HCID 6857587, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 1,2,3,4,8,12,13,14,15,19-deca(4′-t-butylphenylthio)-6,10,17,21-tetrahydro-6,10,17,21-tetra(2′,6′-dimethylphenyl)nonacene-6,10,17,21-tetraol (0.04 g, 0.015 mmol) in 1,4-dioxane (10 mL) was added anhydrous SnCl2 (0.1 g, 0.52 mmol). To this suspension was added 10% HCl (1 mL) in complete darkness and the resulting mixture was stirred at room temperature for 0.5 h under Ar. Upon completion of the reaction, black precipitates were filtered in the dark light under N2. The solids were washed with water (50 mL) followed by methanol to yield persistent nonacene derivative 1,2,3,4,8,12,13,14,15,19-deca(4′-t-butylphenylthio)-6,10,17,21-tetra(2′,6′-dimethylphenyl)nonacene as a black solid. 1H NMR (500 MHz, CDCl3): δ 8.83 (s, 4H), 8.74 (s, 4H), 7.14 (m, 20H), 7.08 (m, 10H), 7.00 (m, 10H), 6.72 (m, 8H), 6.66 (m, 4H), 1.96 (s, 24H), 1.23 (bs, 90H). 13C NMR (125.68 MHz, CDCl3): δ 148.9, 148.7, 148.5, 148.4, 143.5, 143.4, 142.9, 137.7, 137.1, 136.0, 134.2, 133.7, 131.4, 131.3, 130.9, 128.7, 128.4, 128.2, 128.0, 127.9, 127.5, 127.2, 126.1, 126.1, 126.0, 126.0, 34.50, 34.48, 31.51, 31.45, 31.4, 19.9. LDI-MS m/z: 2536 [M+], UV-vis λmax (nm): 550, 600, 655, 716, 846, 921, 1033. The 1H NMR spectrum of 1,2,3,4,8,12,13,14,15,19-deca(4′-t-butylphenylthio)-6,10,17,21-tetra(2′,6′-dimethylphenyl)nonacene and the compound structure are shown in FIGS. 17A & B.

Workup

  1. customUpon completion of the reaction
  2. customblack precipitates
  3. filtrationwere filtered in the dark light under N2
  4. washThe solids were washed with water (50 mL)

Sources & evidence

ORD record
ord-f8e3e359e58247d79e02a1c2118eca17
Source dataset
uspto-grants-2014_09
Patent number
US08822731B2

Reaction notes

Loading…