Water → HCID 9908908, compound

HRID 400124Notes

Reaction equation

HRID 400124 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([O:26][CH2:27][CH3:28])[C:23]([NH2:25])=O)=[CH:17][CH:16]=1)[CH3:11].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1.O>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([O:26][CH2:27][CH3:28])[C:23]([NH2:25])=[S:38])=[CH:17][CH:16]=1)[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 18794821HCID 18794821, compound

Product 1

HCID 9908908HCID 9908908, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-[4-[2-[N-(2-Benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-ethoxypropanamide (428 mg, 1.1 mmol) was suspended in toluene and Lawesson's reagent (1.1 eq) added. After 3 h at refluxed the suspension was cooled and poured into water. After extraction with chloroform (×3) the extracts were washed with aqueous ammonia, dried and concentrated. Chromatography (methanol/dichloromethane) gave the product as a white solid m.p.=46°-48° C.

Workup

  1. temperatureAfter 3 h at refluxed the suspension
  2. temperaturewas cooled
  3. extractionAfter extraction with chloroform (×3) the extracts
  4. washwere washed with aqueous ammonia
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-94948eaa9297498290af290e95acf259
Source dataset
uspto-grants-1998_10
Patent number
US05827865

Reaction notes

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