Ethanolamine → 2,2'-[(2-Nitroethene-1,1-diyl)diazanediyl]di(ethan-1-ol)

HRID 462435Notes

Reaction equation

HRID 462435 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].CS[C:7](SC)=[CH:8][N+:9]([O-:11])=[O:10]>C1(C)C=CC=CC=1>[OH:4][CH2:3][CH2:2][NH:1][C:7]([NH:1][CH2:2][CH2:3][OH:4])=[CH:8][N+:9]([O-:11])=[O:10]

Participants

4

Procedure

78 ml of 2-aminoethanol (1.3 moles) were added slowly over half an hour to a solution of 95 g of 1,1-bis(methylthio)-2-nitroethene (0.57 mole) in 500 ml of toluene at 80° C. After the addition, the mixture was held at 80° C. for half an hour, was cooled to room temperature and the solid formed was filtered off, washed with chloroform (2×100 ml portions) and was dried to give 107 g N,N'-bis(2-hydroxyethyl)-2-nitro-1,1-ethenediamine (97-98% yield) in yellowish crystal form. m.p. 145°-146° C.

Workup

  1. additionAfter the addition
  2. waitthe mixture was held at 80° C. for half an hour
  3. customthe solid formed
  4. filtrationwas filtered off
  5. washwashed with chloroform (2×100 ml portions)
  6. customwas dried

Sources & evidence

ORD record
ord-e5dd896036b144c3a0fcfee571887322
Source dataset
uspto-grants-1985_05
Patent number
US04515806

Reaction notes

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