N-[1-(1-benzothiophen-2-yl)ethyl]hydroxylamine → HCID 10516789, compound

HRID 1655405Notes

Reaction equation

HRID 1655405 reaction equation
[S:1]1[C:5]([CH:6]([NH:8][OH:9])[CH3:7])=[CH:4][C:3]2[CH:10]=[CH:11][CH:12]=[CH:13][C:2]1=2.O([NH:21][C:22]([NH:24][C:25](N)=[O:26])=[O:23])C1C=CC=CC=1>O1CCOCC1>[C:22]([NH:24][C:25](=[O:26])[N:8]([OH:9])[CH:6]([C:5]1[S:1][C:2]2[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=2[CH:4]=1)[CH3:7])(=[O:23])[NH2:21]

Participants

4

Reactant 2

HCID 3692736N-[1-(1-benzothiophen-2-yl)ethyl]hydroxylamineHCID 19792232HCID 19792232, compound

Product 1

HCID 10516789HCID 10516789, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of urea (7.27 g, 119 mmol) was added phenyl chloroformate (8.9 g, 57 mmol) followed by pyridine (30 mL). The resulting mixture became highly exothermic and soon solidified. This solid residue was dispersed and washed well with pyridine and ethylacetate to afford the intermediate N-phenoxycarbamoyl urea. A solution of N-(1-benzo[b]thien-2-yl)ethylhydroxylamine (0.50 g, 2.6 mmol) and N-phenoxycarbamoyl urea (0.46 g, 2.6 mmol) in dioxane (12 mL) was heated at 50° C. for 18 h. The mixture was then brought to 75° C. for 24 h. The reaction was cooled to r.t. and concentrated in vacuo. The resulting residue was crystallized in ethanol:hexanes to afford the desired product. (R1 =NHCONH2, A=CHCH3, X=S [2-isomer], Y=H, M=H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was crystallized in ethanol

Sources & evidence

ORD record
ord-816d7f365d154d989895d3337c978895
Source dataset
uspto-grants-1993_10
Patent number
US05250565

Reaction notes

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