Dihexylamine → HCID 68409704, compound

HRID 1176173Notes

Reaction equation

Br[C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5]([Br:11])=[CH:4][CH:3]=1.[CH2:12]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C=O)C.C1(C)C=CC=CC=1>[Br:11][C:5]1[C:6]2[C:10](=[N:9][S:8][N:7]=2)[C:2]([N:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 160 °C

Procedure

4,7-Dibromobenzo[c][1,2,5]thiadiazole (0.500 g, 1.70×10−3 mol), N,N-dihexylamine (0.50 ml, 2.1×10−3 mol), Pd2dba3 (45 mg, 4.9×10−5 mol), 2-(di-t-butylphosphino)biphenyl (30 mg, 1.0×10−4 mol), NaOt-Bu (0.242 g, 2.5×10−3 mol), toluene (4.0 ml) and DMF (0.40 ml) were added to a reaction vial. The reaction mixture was stirred at 160° C. for 15 min under microwave irradiation. After the reaction mixture was filtered and the solvent was evaporated, the residue was chromatographed on silica gel with 1:1 hexane:CH2Cl2. Yield=0.271 g (40% based on 0.500 g of 4,7-dibromobenzo[c][1,2,5]thiadiazole). 1H NMR (250 MHz, CDCl3): δ 7.59 (d, 1H, J=8.4 Hz, Ph-H), 6.31 (d, 1H, J=8.5 Hz, Ph-H), 3.68 (t, 4H, J=7.7 Hz, —NCH2), 1.51-1.75 (m, 4H, —NCH2CH2—), 1.20-1.44 (m, 12H, —CH2—), 0.89 (t, 6H, J=6.7 Hz, —CH3). CI MS m/z: 398.125 ((M+H)+) (calcd 398.127).

Workup

filtrationAfter the reaction mixture was filtered
customthe solvent was evaporated
customthe residue was chromatographed on silica gel with 1:1 hexane

Sources & evidence

ORD record: ord-34cdcf07590142e5a4919bc64f574c69
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842758B2

Reaction notes

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