Potassium Hydroxide → 4,9-Dihydro-s-indaceno[1,2-b:5,6-b']dithiophene

HRID 1473809Notes

Reaction equation

O.NN.[S:4]1[CH:8]=[CH:7][C:6]2[C:9](=O)[C:10]3[C:22]([C:5]1=2)=[CH:21][C:13]1[C:14](=O)[C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:12]=1[CH:11]=3.[OH-].[K+].N.O>C(O)COCCO>[S:4]1[CH:8]=[CH:7][C:6]2[CH2:9][C:10]3[C:22]([C:5]1=2)=[CH:21][C:13]1[CH2:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:12]=1[CH:11]=3

Participants

Conditions

Temperature: 180 °C

Procedure

Hydrazine hydrate (11.9 cm3, 245 mmol) is added to a suspension of 4,9-dihydro-s-indaceno[1,2-b:5,6-b′]dithiophene-4,9-dione (9.6 g, 32.6 mmol) and KOH (5.5 g, 97.8 mmol) in diethylene glycol (100 cm3). The mixture is heated to 180° C. for 6 hours, and then allowed to cool to 23° C. overnight. NH3/H2O (1:1, 200 cm3) is added and the mixture is stirred for 30 minutes. The solid is collected by filtration, washed with H2O (2×300 cm3) and IMS (2×300 cm3), and dried under vacuum to yield the product as a brown solid (6.89 g, 79%). 1H NMR (300 MHz, d6-DMSO): δ(ppm) 7.71 (s, 2H, Ar—H), 7.55 (d, J=4.9 Hz, 2H), 7.21 (d, J=4.9 Hz, 2H, Ar—H), 3.77 (s, 4H, CH2).

Workup

temperatureto cool to 23° C. overnight
filtrationThe solid is collected by filtration
washwashed with H2O (2×300 cm3) and IMS (2×300 cm3)
customdried under vacuum

Sources & evidence

ORD record: ord-850818b362124741bb7fe93cfe865bf1
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09017577B2

Reaction notes

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