Thionyl Chloride → HCID 10879289, compound

HRID 392060Notes

Reaction equation

HRID 392060 reaction equation
[CH:1]1[C:14]2[N:13]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)S[C:5]=2[CH:4]=[CH:3][CH:2]=1.N=CCCC(CC1C=CC=CC=1)(CC1C=CC=CC=1)O.S(Cl)(Cl)=O>C1C=CC=CC=1>[C:12]1([N:13]([C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 1114022010H-Phenothiazine-10-butanolHCID 22662683HCID 22662683, compound

Product 1

HCID 10879289HCID 10879289, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To prepare compounds 6a, 6b and 6e, to a solution of 5a (2.03 g, 7.5 mmol), 5b or 5e in 100 ml of dry benzene was added thionyl chloride (2 ml, 10 mmol) and stirred overnight at room temperature. After solvent evaporation, the residue was chromatographed on silica gel column. Elution with 10% ethyl acetate/hexanes afforded the following compounds:

Workup

  1. customAfter solvent evaporation
  2. customthe residue was chromatographed on silica gel column
  3. washElution with 10% ethyl acetate/hexanes
  4. customafforded the following compounds

Sources & evidence

ORD record
ord-735e3cac9b934c0f8773f833d4f12b59
Source dataset
uspto-grants-2004_10
Patent number
US06800618B2

Reaction notes

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