Hydrochloric Acid → 1-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-cyanopyrrole

HRID 1871107Notes

Reaction equation

HRID 1871107 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[C:21]([Cl:32])=[C:22]([N:27]2[CH:31]=[CH:30][CH:29]=[CH:28]2)[CH:23]=[CH:24][C:25]=1[Cl:26])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClS([N:37]=[C:38]=O)(=O)=O.CN(C)C=O.Cl>ClCCl>[Si:1]([O:18][CH2:19][C:20]1[C:21]([Cl:32])=[C:22]([N:27]2[CH:31]=[CH:30][CH:29]=[C:28]2[C:38]#[N:37])[CH:23]=[CH:24][C:25]=1[Cl:26])([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 183219091-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)pyrrole

Product 1

HCID 183218191-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-cyanopyrrole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]pyrrole (1.20 g) in anhydrous dichloromethane (12 ml) was added a solution of chlorosulfonyl isocyanate (0.28 ml) in anhydrous dichloromethane (2.8 ml) dropwise in a dry ice-carbon tetrachloride bath. The mixture was stirred at the same temperature for 30 minutes and then at ambient temperature for additional 1 hour. Anhydrous dimethylformamide (0.4 ml) was added to this mixture dropwise in a dry ice-carbon tetrachloride bath. After stirring at the same temperature for 30 minutes and at ambient temperature for additional 1 hour, the reaction mixture was treated with 4N-hydrochloric acid under ice-water cooling for 30 minutes. The organic layer was isolated and the aqueous layer was extracted with chloroform twice. The combined organic phases were washed with saturated aqueous sodium hydrogen carbonate, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluted with n-hexane-ethyl acetate to give 1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]-2-cyanopyrrole (930 mg) as a pale yellow oil.

Workup

  1. waitat ambient temperature for additional 1 hour
  2. stirringAfter stirring at the same temperature for 30 minutes and at ambient temperature for additional 1 hour
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer was extracted with chloroform twice
  5. washThe combined organic phases were washed with saturated aqueous sodium hydrogen carbonate
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by a silica gel column chromatography
  9. washeluted with n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-a436919f4aff41f5acbdb051ee3b4a1c
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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