Thionyl Chloride → HCID 19603735, compound

HRID 1604683Notes

Reaction equation

HRID 1604683 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([CH2:29]O)=[CH:26][CH:27]=5)[C:22]([C:31]#[N:32])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:35])=O>C(Cl)(Cl)Cl>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([CH2:29][Cl:35])=[CH:26][CH:27]=5)[C:22]([C:31]#[N:32])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19603770HCID 19603770, compound

Product 1

HCID 19603735HCID 19603735, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-(hydroxymethyl)indole-3-carbonitrile (0.66 g) and thionyl chloride (0.5 ml) in chloroform (20 ml) was stirred at room temperature for 3 hours. After neutralization with aqueous sodium hydrogen carbonate, the resulting mixture was extracted with chloroform. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure to give 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-(chloromethyl)indole-3-carbonitrile (0.67 g).

Workup

  1. extractionAfter neutralization with aqueous sodium hydrogen carbonate, the resulting mixture was extracted with chloroform
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bc6a215c286841cc851fffda0733992d
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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