Diethanolamine → HCID 69083998, compound

HRID 1503199Notes

Reaction equation

HRID 1503199 reaction equation
[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([O:17][CH2:18][CH2:19][CH2:20]I)=[CH:4][CH:3]=1.[NH:22]([CH2:26][CH2:27][OH:28])[CH2:23][CH2:24][OH:25]>C(#N)C>[OH:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][OH:28])[CH2:20][CH2:19][CH2:18][O:17][C:5]1[C:6]2[S:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14](=[O:16])[C:15]=2[C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 69083376HCID 69083376, compound

Product 1

HCID 69083998HCID 69083998, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Crude 1-chloro-4-(3-iodopropoxy)-9H-thioxanthen-9-one (10.0 g; 23.22 mmol) from the previous step was slowly charged into a solution of diethanolamine (14.65 g; 139.3 mmol) in acetonitrile (100 mL) heated to 50° C. The reaction mixture was stirred vigorously and heated to 50° C. for 60 h. The solvent was removed in vacuo and water (500 mL) was added. The mixture was extracted with dichloromethane (3×250 mL). The aqueous phase was discarded and the organic phase was extracted with hydrochloric acid (2M, 3×100 mL). The pH of the strongly acidic aqueous phase was adjusted to 12-13 by slow addition of 50% aq. NaOH to reprecipitate the product. The aqueous phase was reextracted with dichloromethane (4×100 mL), the organic phase dried (MgSO4), evaporated to give 4-{3-[bis(2-hydroxyethyl)amino]propoxy}-1-chloro-9H-thioxanthen-9-one (5.31 g; 56% yield).

Workup

  1. temperatureheated to 50° C. for 60 h
  2. customThe solvent was removed in vacuo and water (500 mL)
  3. additionwas added
  4. extractionThe mixture was extracted with dichloromethane (3×250 mL)
  5. extractionthe organic phase was extracted with hydrochloric acid (2M, 3×100 mL)
  6. additionThe pH of the strongly acidic aqueous phase was adjusted to 12-13 by slow addition of 50% aq. NaOH
  7. dry with materialthe organic phase dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-e2c81be599484108961ea6ff868d0b7a
Source dataset
uspto-grants-2015_12
Patent number
US09212160B2

Reaction notes

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