5-(2-Amino-1-hydroxyethyl)-1,3-benzenediol → HCID 70376391, compound

HRID 1721967Notes

Reaction equation

HRID 1721967 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9]/[CH:10]=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][CH:13]=1.[NH2:23][CH2:24][CH:25]([C:27]1[CH:28]=[C:29]([OH:34])[CH:30]=[C:31]([OH:33])[CH:32]=1)[OH:26]>CN(C=O)C>[OH:33][C:31]1[CH:32]=[C:27]([CH:25]([OH:26])[CH2:24][NH:23][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9]/[CH:10]=[CH:11]\[C:12]2[CH:17]=[CH:16][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][CH:13]=2)[CH:28]=[C:29]([OH:34])[CH:30]=1

Participants

4

Reactant 2

HCID 125345195-(2-Amino-1-hydroxyethyl)-1,3-benzenediolHCID 13920680HCID 13920680, compound

Product 1

HCID 70376391HCID 70376391, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Z)-N-[4-[3-[(6-Bromohexyl)oxy]-1-propenyl]phenyl]methanesulphonamide (1.56 g) was added portionwise over 10 min to a stirred solution of 5-(2-amino-1-hydroxyethyl)-1,3-benzenediol (1.01 g) and DEA (1.55 g) in dry DMF (20 ml) heated to 80° under nitrogen. When the addition was complete, the mixture was stirred at 80° for 2 h, cooled and evaporated onto `flash` silica. The impregnated material was purified by FCC eluting with System C (39:10:1) to give the title compound as a pale brown powder which was dried in vacuo at 50° for 6 h (0.75 g) m.p. 79°-82°.

Workup

  1. temperatureheated to 80° under nitrogen
  2. additionWhen the addition
  3. temperaturecooled
  4. customevaporated onto `flash` silica
  5. customThe impregnated material was purified by FCC
  6. washeluting with System C (39:10:1)

Sources & evidence

ORD record
ord-d619c90781004ac898525403a181c3ed
Source dataset
uspto-grants-1989_08
Patent number
US04853381

Reaction notes

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