Trimethyl orthoformate → [3-(1,1-Dimethoxyethyl)-5-pentafluorosulfanylphenyl]dimethylamine

HRID 1258501Notes

Reaction equation

HRID 1258501 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[CH:4]=[C:5]([C:15](=[O:17])[CH3:16])[CH:6]=[C:7]([S:9]([F:14])([F:13])([F:12])([F:11])[F:10])[CH:8]=1.[CH:19](OC)(OC)[O:20]C.[CH:26]([O-])([O-])[O-]>CO.CC1(C)[C@]2(CS(O)(=O)=O)C(C[C@H]1CC2)=O>[CH3:26][O:17][C:15]([C:5]1[CH:4]=[C:3]([N:2]([CH3:1])[CH3:18])[CH:8]=[C:7]([S:9]([F:10])([F:11])([F:12])([F:13])[F:14])[CH:6]=1)([O:20][CH3:19])[CH3:16]

Participants

6

Reactant 3

HCID 9005Trimethyl orthoformateHCID 21585117OrthoformateHCID 580857071-(3-Dimethylamino-5-pentafluorosulfanylphenyl)ethanone

Product 1

HCID 58085701[3-(1,1-Dimethoxyethyl)-5-pentafluorosulfanylphenyl]dimethylamineYield 96.9%

Reagents, catalysts & solvents 2

HCID 65617D-Camphorsulfonic AcidCatalystHCID 887MethanolSolvent

Procedure

1-(3-Dimethylamino-5-pentafluorosulfanylphenyl)ethanone (650 mg) was dissolved in methanol (50 ml) and admixed while stirring with trimethyl orthoformate (715 mg) and DL-10-camphorsulfonic acid (10 mg). After stirring for 3 h, more orthoformate (200 mg) was added, and the mixture was stirred for 2 h and left to stand overnight. Then the solvent was drawn off and the residue was dried under high vacuum. 730 mg of crude product were obtained, which were converted directly in the next stage.

Workup

  1. stirringthe mixture was stirred for 2 h
  2. waitleft
  3. waitto stand overnight
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-bccb5caca9234fdf82c95070375a55d5
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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