3-Amino-1,2-propanediol → 2-[3,5-Bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]-N-(2,3-dihydroxypropyl)-acetamide

HRID 2086110Notes

Reaction equation

HRID 2086110 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:10]([CH2:20][C:21](OCC)=[O:22])[N:9]=1.[NH2:26][CH2:27][CH:28]([OH:31])[CH2:29][OH:30]>C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:10]([CH2:20][C:21]([NH:26][CH2:27][CH:28]([OH:31])[CH2:29][OH:30])=[O:22])[N:9]=1

Participants

4

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 135914986Ethyl [3,5bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetate

Product 1

HCID 1358174672-[3,5-Bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]-N-(2,3-dihydroxypropyl)-acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.0 g of ethyl [3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetate (Example 2) and 2.4 g of (±)3-amino-1,2-propanediol are heated at 60° C. for 2 h in 10 ml of ethanol. The crystals precipitating on cooling are filtered off and washed with ethanol. After drying, 2-[3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]-N-(2,3-dihydroxypropyl)acetamide remains as colorless crystals of m.p. 180-181° C.

Workup

  1. customThe crystals precipitating
  2. temperatureon cooling
  3. filtrationare filtered off
  4. washwashed with ethanol
  5. customAfter drying

Sources & evidence

ORD record
ord-4da0a866eb314263877c4dd24174fd90
Source dataset
uspto-grants-2004_04
Patent number
US06723742B2

Reaction notes

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