Ethanolamine → HCID 21523506, compound

HRID 918201Notes

Reaction equation

HRID 918201 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[CH2:4][N:5]=[C:6]=[S:7].[CH2:13]([CH2:15][NH2:16])[OH:14]>C(O)(C)C.C1C=CC=CC=1>[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[CH2:4][NH:5][C:6]([NH:16][CH2:15][CH2:13][OH:14])=[S:7]

Participants

5

Reactant 2

HCID 700Ethanolamine2×HCID 21523505HCID 21523505, compound

Product 1

HCID 21523506HCID 21523506, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 3776IsopropanolSolvent2×

Procedure

2,4-Dimethylbenzyl isothiocyanate (15.7 grams; 0.08 mole) was mixed with 23 milliliters (ml) of isopropyl alcohol and a solution of ethanolamine (5.8 grams; 0.08 mole) in 23 ml of isopropyl alcohol added dropwise thereto with stirring. The temperature of the reaction mixture was maintained below about 50°C during the ethanolamine addition and then stirred at ambient temperatures for a period of about 16 hours. The reaction mixture was then concentrated to dryness and the residue obtained taken up in benzene. The resulting benzene solution was cooled to give crystals which were filtered off. The title product was thus obtained in about a 58% yield as a crystalline solid having a melting point of 101-103°C.

Workup

  1. stirringstirred at ambient temperatures for a period of about 16 hours
  2. concentrationThe reaction mixture was then concentrated to dryness
  3. customthe residue obtained
  4. customto give crystals which
  5. filtrationwere filtered off

Sources & evidence

ORD record
ord-2c789785f34d47bc9ab8eb166db8a9e5
Source dataset
uspto-grants-1976_07
Patent number
US03969532

Reaction notes

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