Sulfuric Acid → HCID 20504286, compound

HRID 1702158Notes

Reaction equation

[Na].[C:2]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)#[CH:3].C[O-].[Na+].[N+]([C:17]1[CH:18]=[C:19]2[C:24](=[O:25])[N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[CH:33])[CH:27]=3)[C:21](=[O:22])[C:20]2=[CH:34][CH:35]=1)([O-])=O.S(=O)(=O)(O)O>C(Cl)Cl.CCCCCC.CN(C)C(=O)C>[C:2]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][C:17]1[CH:18]=[C:19]2[C:24](=[O:25])[N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[CH:33])[CH:27]=3)[C:21](=[O:22])[C:20]2=[CH:34][CH:35]=1)#[CH:3]

Participants

Conditions

Temperature: 70 °C

Procedure

To the sodium salt of 3-ethynylphenol, prepared from 4.3 g (0.037 mole) of sodium methoxide was added 50 ml of dry N,N-dimethylacetamide, under nitrogen. The mixture was heated to 70° C. and 12.0 g (0.041 mole) of 4-nitro-N-(3-ethynylphenyl)-phthalimide was added. The dark mixture was stirred at 70° C. for 3 hours, then poured into 1.5 liters of ice water. About 100 ml of 1 N sulfuric acid was added to the cold mixture to precipitate the product. The precipitate was collected by filtration, air dried, dissolved in 100 ml of methylene chloride, than again filtered. Chromotography of the filtrate on silica gel using 1:1 hexane:methylene chloride as the eluent gave 5.8 g (44% yield) of product, m.p. 150°-160° C.

Workup

customto precipitate the product
filtrationThe precipitate was collected by filtration, air
customdried
dissolutiondissolved in 100 ml of methylene chloride
filtrationthan again filtered

Sources & evidence

ORD record: ord-62834feebfdf41e9921aed8a453ca008
Source dataset: uspto-grants-1983_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04380619

Reaction notes

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