Ethanolamine → HCID 86622763, compound

HRID 1020264Notes

Reaction equation

HRID 1020264 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15]I)[N:14]=1)=[O:8].[NH2:21][CH2:22][CH2:23][OH:24].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][NH:21][CH2:22][CH2:23][OH:24])[N:14]=1)=[O:8]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 962WaterHCID 58055059HCID 58055059, compound2×

Product 1

HCID 86622763HCID 86622763, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3,4-dichlorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea (Intermediate XXII) was taken up in THF and an excess of the 2-Amino-ethanol (20 equiv.) was added. The reaction was allowed to stir overnight at room temperature. Reaction poured into water and extracted with ethyl acetate, partitioned with brine, dried over NaSO4, filtered, and volatiles were removed in vacuo. The resulting solid was triturated with ethyl acetate, followed by diethyl ether to give the title compound. 1H NMR (400 MHz, CD3OD): 7.50-7.45 (m, 2H), 7.26 (dd, 1H), 6.78 (s, 1H), 4.41 (s, 2H), 3.73 (s, 2H), 3.65 (t, 2H), 2.71 (t, 2H). MS (ES+): M/Z 375 and 377 (M+1).

Workup

  1. customReaction
  2. extractionextracted with ethyl acetate
  3. custompartitioned with brine
  4. dry with materialdried over NaSO4
  5. filtrationfiltered
  6. customvolatiles were removed in vacuo
  7. customThe resulting solid was triturated with ethyl acetate

Sources & evidence

ORD record
ord-0bcf118631424f68ac5b317637b6f4e4
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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