Cesium carbonate → N-(benzhydrylideneamino)-2-[(E)-(benzhydrylidenehydrazinylidene)methyl]thiophen-3-amine

HRID 2173031Notes

Reaction equation

Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1/[CH:7]=[N:8]/[N:9]=[C:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:23]1([C:29](=[N:36][NH2:37])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:11]1([C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:9]/[N:8]=[CH:7]/[C:3]2[S:4][CH:5]=[CH:6][C:2]=2[NH:37][N:36]=[C:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a mixture of (E)-1-((3-bromothiophen-2-yl)methylene)-2-(diphenylmethylene)hydrazine (15 g, 40.6 mmol, including its Z isomer) and (diphenylmethylene)hydrazine (9.57 g, 48.7 mmol) in toluene (125 mL) was added palladium(II) acetate (0.120 g, 2.031 mmol), 1,1′-bis(diphenylphosphino)ferrocene (2.252 g, 4.06 mmol) and Cs2CO3 (26.5 g, 81 mmol). The reaction mixture was stirred at 85° C. for 14 hours and was subsequently diluted with toluene (25 mL) and filtered to remove undissolved solids. The filtrate was purified by flash column chromatography. The pure product fractions were evaporated to give the title compound (15.5 g, 79%). ESI-MS m/z [M+H]+ calc'd for C31H24N4S, 485. found, 485.

Workup

filtrationfiltered
customto remove undissolved solids
customThe filtrate was purified by flash column chromatography
customThe pure product fractions were evaporated

Sources & evidence

ORD record: ord-99fcdd3a670c4a1eb20e558b7eb908b8
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056873B2

Reaction notes

Loading…