2-(Dimethylamino)ethanol → HCID 13672821, compound

HRID 1732016Notes

Reaction equation

HRID 1732016 reaction equation
[CH:1]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]([C:15]([OH:17])=[O:16])[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21]O>S(Cl)(Cl)=O.C1C=CC=CC=1>[CH:1]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]([C:15]([O:17][CH2:21][CH2:20][N:19]([CH3:23])[CH3:18])=[O:16])[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 13672818HCID 13672818, compound

Product 1

HCID 13672821HCID 13672821, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

6H-dibenzo[b,d]thiopyran-6-carboxylic acid (3.4 g; 0.014 mol) was suspended in thionyl chloride (30 ml) and after 20 hours at room temperature the solution was evaporated in vacuo. The crude residue was dissolved in 80 ml of benzene and the obtained solution was added dropwise, at room temperature, to a solution of 2-dimethylaminoethanol (42 ml; 0.042 mol) in 80 ml of benzene. After half an hour the solution was washed with water and dried over sodium sulfate and concentrated to dryness. 6H-dibenzo[b,d]thiopyran-6-carboxylic acid, 2-dimethylamino-ethyl ester was obtained as oil; (3.0 g; yield 70%); NMR (CDCl3) δ ppm: 2.12 (s) (6H,CH3), 2.37 (t) (2H, --CH2NMe2), 4.07 (t) (2H, COOCH2), 4.59 (s) (1H,C-6 proton), 7.1-7.5 (m) (6H; C-2, C-3, C-4, C-7, C-8 and C-9 phenyl protons), 7.78 (m) (2H; C-1 and C-10 phenyl protons). By proceeding analogously the following compounds were obtained:

Workup

  1. customthe solution was evaporated in vacuo
  2. dissolutionThe crude residue was dissolved in 80 ml of benzene
  3. washAfter half an hour the solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cf0985495385468b8088e746ba20fa71
Source dataset
uspto-grants-1986_11
Patent number
US04624949

Reaction notes

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