Ethanolamine → HCID 13720648, compound

HRID 1680192Notes

Reaction equation

HRID 1680192 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([C:12]([S:14]C)=S)[CH2:11][CH2:10][CH2:9][S:8]1.[CH2:16]([CH2:18][NH2:19])[OH:17]>C(O)C>[OH:17][CH2:16][CH2:18][NH:19][C:12]([C:7]1([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:11][CH2:10][CH2:9][S:8]1)=[S:14]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 13720640HCID 13720640, compound

Product 1

HCID 13720648HCID 13720648, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 2-(pyrid-2-yl)tetrahydrothiophene-2-carbodithioate (12.8 g) and ethanolamine (3 g) in ethanol (150 cc) is heated under reflux for 1 hour 30 minutes. After concentrating the reaction mixture to dryness (20 mm Hg; 2.7 kPa) at 50° C., the resulting residue (14.8 g) is dissolved in boiling ethanol (80 cc) and the solution, to which decolourising charcoal (0.3 g) is added, is filtered hot and then kept, after cooling, for 1 hour at a temperature of about 0° C. The crystals which have appeared are filtered off, washed twice with ethanol (30 cc in total) and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 50° C. N-(2-Hydroxyethyl)-2-(pyrid-2-yl)tetrahydrothiophene-2-carbothioamide (11.4 g), melting at 132° C., is thus obtained.

Workup

  1. temperatureunder reflux for 1 hour 30 minutes
  2. concentrationAfter concentrating the reaction mixture to dryness (20 mm Hg; 2.7 kPa) at 50° C.
  3. dissolutionthe resulting residue (14.8 g) is dissolved
  4. additionis added
  5. filtrationis filtered hot
  6. filtrationThe crystals which have appeared are filtered off
  7. washwashed twice with ethanol (30 cc in total)
  8. customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 50° C

Sources & evidence

ORD record
ord-eefe689414cd4d6ea1c6a4d8e2b96a37
Source dataset
uspto-grants-1981_06
Patent number
US04272534

Reaction notes

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