Acetic Acid → HCID 178467281, compound

HRID 1199490Notes

Reaction equation

HRID 1199490 reaction equation
[CH:1]1[C:6]([O-:7])=[CH:5][C:4]2[O:8][C:9]3[C:15](=[N+:16]([O-])[C:3]=2[CH:2]=1)[CH:14]=[CH:13][C:11](=[O:12])[CH:10]=3.[Na+].C(O[C:23](=[O:25])[CH3:24])(=O)C.[C:26]([OH:29])(=O)[CH3:27].CO.C(Cl)(Cl)Cl.[C:36](OCC)(=[O:38])[CH3:37]>>[C:36]([C:5]1[C:4]2[O:8][C:9]3[C:15](=[CH:14][CH:13]=[C:11]([OH:12])[CH:10]=3)[NH:16][C:3]=2[C:2]([C:26](=[O:29])[CH3:27])=[C:1]([C:23](=[O:25])[CH3:24])[C:6]=1[OH:7])(=[O:38])[CH3:37]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 7918Acetic AnhydrideHCID 1129393H-Phenoxazin-3-one, 7-hydroxy-, 10-oxide, sodium saltHCID 21584013Chloroform ethylacetate

Product 1

HCID 178467281HCID 178467281, compound

Procedure

2.51 g. (10 mmole) resazurin sodium salt and 4.17 g. (22 mmole) stannous chloride were heated under reflux for 1 hour in a mixture of 6.7 ml. (72 mmole) acetic anhydride and 8 ml. glacial acetic acid, a clear brown solution gradually being formed. About 30 ml. methanol were then added thereto in an ice bath, while stirring, spontaneous crystallisation thereby taking place. After 20 hours at 0° C., the crystals were filtered off with suction, washed with ice cold isopropanol and petroleum ether and dried in a vacuum over anhydrous calcium chloride. There were obtained 2.64 g. (77% of theory) of beige coloured needles; m.p. 208° C. Rf value: 0.45 (TLC on silica gel; chloroform/ethyl acetate 2:1 v/v).

Workup

  1. temperatureunder reflux for 1 hour in a mixture of 6.7 ml
  2. customspontaneous crystallisation
  3. filtrationthe crystals were filtered off with suction
  4. washwashed with ice cold isopropanol and petroleum ether
  5. dry with materialdried in a vacuum over anhydrous calcium chloride
  6. customThere were obtained 2.64 g

Sources & evidence

ORD record
ord-64f8d3e4bade4702b2f2d9165330d2ea
Source dataset
uspto-grants-1990_02
Patent number
US04900822

Reaction notes

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