Ethanol → HCID 19701078, compound

HRID 861919Notes

Reaction equation

HRID 861919 reaction equation
S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[CH3:12][C:13]1[CH:14]=[N+:15]([O-])[C:16]2[C:17](=[O:28])[C:18]3[C:23]([C:24](=[O:27])[C:25]=2[CH:26]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3.[CH2:30]([OH:32])[CH3:31]>>[CH2:30]([O:32][C:14]1[C:13]([CH3:12])=[CH:26][C:25]2[C:24](=[O:27])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:28])[C:16]=2[N:15]=1)[CH3:31]

Participants

4

Reactant 3

HCID 702EthanolHCID 73974-Toluenesulfonyl chlorideHCID 14927368HCID 14927368, compound

Product 1

HCID 19701078HCID 19701078, compoundYield 52%

Procedure

5 portions of 0.08 g (0.42 mmol of tosyl chloride were added to an agitated solution of 100 mg. (0.42 mmol) of 3-methyl-1-azaanthracen-9,10-dione 1-oxide in absolute ethanol at 75°-78° C. for 1 hour. Then the mixture was agitated at room temperature overnight and a yellow solid (58 mg, 0.22 mmol) corresponding to the compound (I-b) (yield 52%) was filtered. The starting product was recovered from the water by means of silica gel column chromatography eluting with ethyl acetate: ethanol (9:1): m.p. 186°-188° C. (the sublime compound around 170° C.).

Workup

  1. customThe starting product was recovered from the water by means of silica gel column chromatography
  2. washeluting with ethyl acetate: ethanol (9:1)
  3. customthe sublime compound around 170° C.

Sources & evidence

ORD record
ord-26ab682d9c4a4d8b9fafda20ccf78b58
Source dataset
uspto-grants-1998_02
Patent number
US05716963

Reaction notes

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