Sodium Bicarbonate → HCID 24852406, compound

HRID 2245374Notes

Reaction equation

HRID 2245374 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-17c4ac89bbfd47f89360befd438facc3
Source dataset
uspto-grants-2010_03
Patent number
US07683084B2

Reaction notes

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