Chlorotrimethylsilane → HCID 22750284, compound

HRID 2164158Notes

Reaction equation

HRID 2164158 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[NH:12][C:13](=[O:20])[C:14](=[CH:18][CH:19]=2)[C:15](O)=O)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].O1CCCC1.C[Si]([Cl:30])(C)C.S(Cl)(Cl)=O>C(N(CC)CC)C>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[NH:12][C:13](=[O:20])[C:14](=[CH:18][CH:19]=2)[CH2:15][Cl:30])[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 22750277HCID 22750277, compound

Product 1

HCID 22750284HCID 22750284, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A stirred suspension of 2.6 g. of 6-[3-(aminosulfonyl)phenyl]-1,2-dihydro-2-oxonicotinic acid in 130 ml. of tetrahydrofuran is treated with 1.24 ml. of triethylamine. After a few minutes, the resulting solution is treated with 1.12 ml. of trimethylsilyl chloride and stirred 1 hour at room temperature. The solution is then treated with 1.28 ml. of thionyl chloride and stirred for 2 hours at room temperature. The resulting solution is diluted with 200 ml. of hexane and the precipitate of 6-[3-aminosulfonyl)phenyl]-1,2-dihydro-2-oxonicotinyl chloride is collected by filtration, washed with hexane and dried. The acid chloride is used as such without further purification.

Workup

  1. additionA stirred suspension of 2.6 g
  2. waitAfter a few minutes
  3. additionthe resulting solution is treated with 1.12 ml
  4. additionThe solution is then treated with 1.28 ml
  5. additionThe resulting solution is diluted with 200 ml
  6. filtrationof hexane and the precipitate of 6-[3-aminosulfonyl)phenyl]-1,2-dihydro-2-oxonicotinyl chloride is collected by filtration
  7. washwashed with hexane
  8. customdried
  9. customsuch without further purification

Sources & evidence

ORD record
ord-7a9aed1df534428d8c32f6a75a296943
Source dataset
uspto-grants-1979_01
Patent number
US04137408

Reaction notes

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