Hydrochloric Acid → HCID 86615526, compound

HRID 1822098Notes

Reaction equation

[Cl:1][C:2]1[CH:23]=[CH:22][C:21]2[C:20](=O)[C:19]3[C:6](=[CH:7][C:8]4[C:9](=O)[C:10]5[C:15]([C:16](=O)[C:17]=4[CH:18]=3)=[CH:14][C:13]([Cl:26])=[CH:12][CH:11]=5)[C:5](=O)[C:4]=2[CH:3]=1.[BH4-].[Na+].CO.Cl>COCCOCCOC.O>[Cl:1][C:2]1[CH:23]=[CH:22][C:21]2[C:4](=[CH:5][C:6]3[C:19]([CH:20]=2)=[CH:18][C:17]2[C:8](=[CH:9][C:10]4[C:15]([CH:16]=2)=[CH:14][C:13]([Cl:26])=[CH:12][CH:11]=4)[CH:7]=3)[CH:3]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of 2.0 grams (5.9 mmol, leq) of 2,9-dichloropentacene-5,7,12,14-tetrone and 3.0 g (322 mmol, 54 eq) of sodium borohydride in 46 mL of 2-methoxyethylether was stirred at 23° C. in a nitrogen atmosphere for 14 hours. To this reaction mixture was added 23 mL of methanol in a dropwise fashion to keep the reaction temperature below 50° C. A solution of 18 grams (96 mmol, 16 eq) of stannous chloride in 19.7 grams of water and 7.3 grams of 12M hydrochloric acid was added at such a rate as to keep the reaction temperature between 23° C. and 40° C. The mixture was stirred for an additional 30 minutes. The reaction mixture was filtered and the residue washed with 46 mL of 12M hydrochloric acid followed by 120 mL of acetone and 40 mL of THF. The solid was dried in air to give 0.95 grams of the desired product. IR KBr 1618 cm−1, 906 cm−1.

Workup

customthe reaction temperature below 50° C
customthe reaction temperature between 23° C. and 40° C
stirringThe mixture was stirred for an additional 30 minutes
filtrationThe reaction mixture was filtered
washthe residue washed with 46 mL of 12M hydrochloric acid
customThe solid was dried in air

Sources & evidence

ORD record: ord-5f1821179a7340ccb78047545a1ae34c
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608679B2

Reaction notes

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