Ammonium Chloride → HCID 23503239, compound

HRID 1835171Notes

Reaction equation

HRID 1835171 reaction equation
[CH2:1]([Li])CCC.Cl[C:7]1[CH:8]=[C:9]([CH2:13][C:14]2[S:18][CH:17]=[C:16]([C:19](O)=[O:20])[C:15]=2[O:22][CH2:23][CH2:24][O:25][Si](C(C)(C)C)(C)C)[CH:10]=[CH:11][CH:12]=1.CO[CH2:35][C:36]([N:38](OC)[CH3:39])=[O:37].[Cl-:42].[NH4+:43]>O1CCCC1>[Cl:42][C:7]1[CH:8]=[C:9]([CH2:13][C:14]2[S:18][C:17]3[C:16]([CH2:19][O:20][CH3:1])=[N:43][N:38]([CH3:39])[C:36](=[O:37])[C:35]=3[C:15]=2[O:22][CH2:23][CH2:24][OH:25])[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 14872187N,2-dimethoxy-N-methylacetamideHCID 235032315-[(3-Chlorophenyl)methyl]4-{2-[(1,1-dimethylethyl)dimethylsilyl]oxyethoxy}thiophene-3-carboxylic acidHCID 178418339Butyllithium

Product 1

HCID 23503239HCID 23503239, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-20 °C

Procedure

2.0M butyl lithium in hexanes (1 ml) was diluted with tetrahydrofuran (3 ml) and cooled to −20° C. 5-[(3-Chlorophenyl)methyl]-4-{2-[(1,1-dimethylethyl)-dimethylsilyl]oxyethoxy}thiophene-3carboxylic acid in tetrahydrofuran (1 ml of 1M solution) was added slowly. The solution was mixed for 10 minutes and then 1 mmol of 2,N-Dimethoxy-N-methylacetamide in 1 ml of tetrahydrofuran was added. The solution was mixed for 10 minutes and was then added to 5 m of ammonium chloride solution. The reaction mixture was evaporated in air for 18 hours. The residue was dissolved in dichloromethane and washed with water twice. The solvent was allowed to evaporate and the residue was then dissolved in 5 ml of ethanol. To this solution was added 92 mg of methyl hydrazine. The resulting solution was heated at reflux for 4 hours. The reaction mixture was allowed to cool and the solvent was evaporated. Purification by column chromatography, eluting with an isohexane:ethyl acetate gradient, gave the title compound (4 mg).

Workup

  1. additionThe solution was mixed for 10 minutes
  2. additionThe solution was mixed for 10 minutes
  3. customThe reaction mixture was evaporated in air for 18 hours
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water twice
  6. customto evaporate
  7. dissolutionthe residue was then dissolved in 5 ml of ethanol
  8. additionTo this solution was added 92 mg of methyl hydrazine
  9. temperatureThe resulting solution was heated
  10. temperatureat reflux for 4 hours
  11. temperatureto cool
  12. customthe solvent was evaporated
  13. customPurification by column chromatography
  14. washeluting with an isohexane

Sources & evidence

ORD record
ord-23425716865a402f82835d1bca90cbb3
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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