Hydrochloric Acid → 7-Hydroxy-1,4-diaza-10H-phenothiazine

HRID 979978Notes

Reaction equation

HRID 979978 reaction equation
[H-].[Na+].C(S)C.C[O:7][C:8]1[CH:9]=[C:10]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[N:16]=[CH:15][CH:14]=[N:13][C:12]=1[S:11]2.Cl>CN(C=O)C>[OH:7][C:8]1[CH:9]=[C:10]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[N:16]=[CH:15][CH:14]=[N:13][C:12]=1[S:11]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 137498967-Methoxy 1,4-diazaphenothiazine

Product 1

HCID 1361490897-Hydroxy-1,4-diaza-10H-phenothiazineYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60 mg, 2.5 mmoles) was added to ethanethiol (124 mg, 2 mmoles) in dry DMF (2 ml) under argon. 7-Methoxy-1,4-diaza-10H-phenothiazine (462 mg, 2 mmoles) was then added and the reaction mixture was refluxed for 3 hours. The mixture was poured into 0.5N HCl (50 ml). The solid was collected, washed with methanol and air-dried to yield starting material. Extraction of the filtrate with ethyl acetate gave 100 mg of a mixture that was chromatographed on silica gel, eluting with 40% ethyl acetate in hexane to yield 25 mg of the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. customThe solid was collected
  3. washwashed with methanol
  4. customair-dried
  5. customto yield
  6. extractionExtraction of the filtrate with ethyl acetate

Sources & evidence

ORD record
ord-b3787ff703164b7597fee75ac695b424
Source dataset
uspto-grants-1987_01
Patent number
US04634766

Reaction notes

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