Ethanolamine → HCID 20063974, compound

HRID 359844Notes

Reaction equation

HRID 359844 reaction equation
[C:1]([O:21]C)(=O)[C:2]1[CH:7]=[CH:6][C:5]([S:8][S:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=O)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH2:23]([CH2:25][NH2:26])[OH:24]>>[OH:24][CH2:23][CH2:25][NH:26][C:14](=[O:16])[C:13]1[CH:12]=[CH:11][C:10]([S:9][S:8][C:5]2[CH:4]=[CH:3][C:2]([C:1]([NH:26][CH2:25][CH2:23][OH:24])=[O:21])=[CH:7][CH:6]=2)=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 3476987Dimethyl 4,4'-disulfanediyldibenzoate

Product 1

HCID 20063974HCID 20063974, compoundYield 68.7%

Conditions

Temperature
140 °C

Procedure

A mixture of 16.5 g of dimethyl 4,4'-dithiobis[benzoate] [Werbel et al., J. Heterocycl. Chem. 17, 497 (1980)] and 13.0 g of ethanolamine was heated at 140° C. while collecting the methanol which distilled from the reaction. After evolution of methanol had ceased, the reaction mixture was cooled and acidified with dilute hydrochloric acid. The solid product which formed was collected and dried to give 13.3 g of N,N'-bis(2-hydroxyethyl)-4,4'-dithiobis[benzamide], used directly in the next reaction.

Workup

  1. customwhile collecting the methanol which
  2. distillationdistilled from the reaction
  3. temperaturethe reaction mixture was cooled
  4. customThe solid product which formed
  5. customwas collected
  6. customdried

Sources & evidence

ORD record
ord-71290c6020314951a05f9fcfaa3ac91f
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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