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

HRID 249714

Reaction equation

HRID 249714 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-pentafluorosulfanyl phenyl)ethanone (650 mg) was dissolved in methanol (50 ml) and treated with 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 then allowed to stand overnight. The solvent was then stripped off and the residue was dried in a high vacuum. 730 mg of crude product were obtained, which were reacted directly in the next stage.

Workup

  1. additiontreated
  2. stirringthe mixture was stirred for 2 h
  3. waitto stand overnight
  4. customthe residue was dried in a high vacuum

Sources & evidence

ORD record
ord-81c31f13f25a4b3e833e94d168e57d8f
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Linked notes

Loading…