1,1,1-Trimethoxybutane → HCID 135677718, compound

HRID 1794603Notes

Reaction equation

HRID 1794603 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([CH3:7])[C:3]=1[C:8]([NH2:10])=[O:9].[C:11](OC)(OC)(OC)[CH2:12][CH2:13][CH3:14]>C(OC(=O)C)(=O)C>[CH3:7][C:4]1[C:3]2[C:8](=[O:9])[NH:10][C:11]([CH2:12][CH2:13][CH3:14])=[N:1][C:2]=2[S:6][N:5]=1

Participants

4

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 122550895-AMINO-3-METHYLISOTHIAZOLE-4-CARBOXAMIDE

Product 1

HCID 135677718HCID 135677718, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 29 (3.0 g, 19.1 mmol), trimethyl orthobutyrate (7.0 mL) in acetic anhydride (7.0 mL) was heated at 130° C. in an open flask for 3 h, then cooled to room temperature and poured into ice water. The mixture was extracted with EtOAc for 3 times. The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography to give 30 (1.6 g, 40%) as a yellow solid. 1H-NMR (400 MHz, CDCl3): δ 12.15 (brs, 1H), 2.81 (s, 3H), 2.78 (t, J=7.68 Hz, 2H), 1.90 (m, 2H), 1.07 (t, J=7.37 Hz, 3H).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with EtOAc for 3 times
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-46df36ad001a40d3b236d844034ce9e5
Source dataset
uspto-grants-2006_04
Patent number
US07022850B2

Reaction notes

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