Sodium Bicarbonate → HCID 24852406, compound

HRID 1260354Notes

Reaction equation

HRID 1260354 reaction equation
[F:1][C:2]1([F:24])[O:6][C:5]2[CH:7]=[CH:8][C:9]([N:11]3[CH:15]=[C:14]([CH2:16]O)[S:13]/[C:12]/3=[N:18]\[C:19](=[O:23])[N:20]([CH3:22])[CH3:21])=[CH:10][C:4]=2[O:3]1.COCCN(S(F)(F)[F:35])CCOC.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1([F:24])[O:6][C:5]2[CH:7]=[CH:8][C:9]([N:11]3[CH:15]=[C:14]([CH2:16][F:35])[S:13]/[C:12]/3=[N:18]\[C:19](=[O:23])[N:20]([CH3:22])[CH3:21])=[CH:10][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 24852301HCID 24852301, compound

Product 1

HCID 24852406HCID 24852406, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N′-[(2Z)-3-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-(hydroxymethyl)-1,3-thiazol-2(3H)-ylidene]-N,N-dimethylurea (Example 87, 0.2 g, 0.56 mmol) in dry CH2Cl2 (10 mL) was treated with bis(2-methoxyethyl)aminosulfur trifluoride (0.148 g, 0.67 mmol). After 4 hours at room temperature, the mixture was neutralized by dropwise addition of a saturated solution of sodium bicarbonate. The mixture was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified over silica using CH2Cl2 as mobile phase. 1H NMR (CDCl3) δ ppm 3.00 (6H), 5.20 (1H), 5.38 (1H), 7.00 (1H), 7.30 (2H), 7.38 (1H); MS (ESI) 360(M+H)+.

Workup

  1. washThe mixture was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified over silica

Sources & evidence

ORD record
ord-de26d8a8f59f41d89cd0099fbbc4f21f
Source dataset
uspto-grants-2013_06
Patent number
US08470813B2

Reaction notes

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