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Water → (2-Butyl-5-methylsulfanylamino-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone

HRID 1771252
Notes
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Reaction equation

HRID 1771252 reaction equation
[CH3:1][S:2]Cl.[NH2:4][C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([CH2:13][CH2:14][CH2:15][CH3:16])=[C:10]([C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][N:29]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33])=[CH:21][CH:20]=3)=[O:18])[C:9]=2[CH:38]=1.C[O-].[Na+].O>CO>[CH2:13]([C:11]1[O:12][C:8]2[CH:7]=[CH:6][C:5]([NH:4][S:2][CH3:1])=[CH:38][C:9]=2[C:10]=1[C:17]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][CH2:28][N:29]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:34][CH2:35][CH2:36][CH3:37])=[CH:23][CH:24]=1)=[O:18])[CH2:14][CH2:15][CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 138595MethanesulfenylchlorideHCID 10942334Sodium MethoxideHCID 11488441(5-Amino-2-butylbenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone

Product 1

HCID 71711318(2-Butyl-5-methylsulfanylamino-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanoneYield 87.1%

Reagents, catalysts & solvents

1
HCID 887MethanolSolvent

Procedure

1.98 g of methanesulfenyl chloride (II) (0.024 mol, 1.2 eq; freshly prepared as described in the above mentioned literature), 9.57 g of (5-amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone (III) (0.02 mol, 1 eq) and 10 mL of 1.5 M sodium methylate methanolic solution were added into a flask and the mixture was diluted with 50 mL of methanol. The reaction mixture was stirred for 3 hours at room temperature. After the reaction was complete (followed by HPLC) the mixture was poured into 150 mL of water. The product was extracted with 2×60 mL of dichloromethane. The organic phase was washed with 50 mL of aq. NaHCO3 solution and then with 50 mL of water. The solvent was evaporated and the product was purified by column chromatography (column: spheric silica (60 Å); eluent: toluene:MTBE:methanol=50:40:10) to obtain 9.14 g of compound (IV) (87%) as a light yellow oil.

Workup

  1. customfreshly prepared
  2. additionwere added into a flask
  3. extractionThe product was extracted with 2×60 mL of dichloromethane
  4. washThe organic phase was washed with 50 mL of aq. NaHCO3 solution
  5. customThe solvent was evaporated
  6. customthe product was purified by column chromatography (column: spheric silica (60 Å); eluent: toluene:MTBE:methanol=50:40:10)

Sources & evidence

ORD record
ord-7d5aa885135d4105a698f7bc42188f04
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249119B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes