Chlorotrimethylsilane → HCID 178479884, compound

HRID 1447425Notes

Reaction equation

HRID 1447425 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:5]=2[C:4]2[O:14][C:15]([C:19](O)=[O:20])=[CH:16][C:17](=[O:18])[C:3]1=2.C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:35][C:36]1[NH:40][N:39]=[N:38][N:37]=1.C(N(CC)CC)C.Cl[Si](C)(C)C>CN(C=O)C>[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:5]=2[C:4]2[O:14][C:15]([C:19]([NH:35][C:36]3[NH:40][N:39]=[N:38][N:37]=3)=[O:20])=[CH:16][C:17](=[O:18])[C:3]1=2

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 12628432HCID 12628432, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178479884HCID 178479884, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 4.7 g (16.4 mmole) 4,5-dihydro-5-methyl-8-nitro-4-oxopyrano[3,2-b]indole-2-carboxylic acid and 3.8 g (23.4 mmole) 1,1'carbonyl-diimidazole in 100 ml DMF was heated at 60° C. for one hour and then cooled to room temperature. In a separate flask, a mixture of 1.8 g (17.5 mmole) 5-aminotetrazole monohydrate and 5.4 g (53.1 mmole) triethylamine were combined in 50 ml DMF. This mixture was cooled in an ice bath while 5.8 g (52.8 mmole) chlorotrimethylsilane was added in one portion. Stirring in ice was continued for one hour, followed by an additional two hours with the ice bath removed. The triethylamine mixture was then added to the original carboxylic acid mixture, and the new mixture was heated on a steam bath for one hour. The mixture was cooled, and the precipitated triethylamine hydrochloride was filtered and discarded. The filtrate was added to 500 g ice/water, the mixture was filtered by gravity, and the filtrate was acidified with 4 N hydrochloric acid. The precipitated crude product was filtered, washed with water and recrystallized twice from DMF-water to yield yellow solid of mp 295° C. dec.

Workup

  1. temperaturecooled to room temperature
  2. additionwas added in one portion
  3. customremoved
  4. additionThe triethylamine mixture was then added to the original carboxylic acid mixture
  5. temperaturethe new mixture was heated on a steam bath for one hour
  6. temperatureThe mixture was cooled
  7. filtrationthe precipitated triethylamine hydrochloride was filtered
  8. additionThe filtrate was added to 500 g ice/water
  9. filtrationthe mixture was filtered by gravity
  10. customThe precipitated crude product
  11. filtrationwas filtered
  12. washwashed with water
  13. customrecrystallized twice from DMF-water
  14. customto yield yellow solid of mp 295° C. dec.

Sources & evidence

ORD record
ord-b0111b42c0ec4cd39961675620ad70aa
Source dataset
uspto-grants-1982_02
Patent number
US04316904

Reaction notes

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