Ethanol → HCID 58055072, compound

HRID 1685004Notes

Reaction equation

HRID 1685004 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[O:10])[S:6][CH:7]=1.[CH3:20][NH:21][O:22][CH3:23].C(=O)([O-])[O-].[Na+].[Na+].CCO>O>[F:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][NH:11][C:9](=[O:10])[NH:8][C:5]1[S:6][CH:7]=[C:3]([CH2:2][N:21]([O:22][CH3:23])[CH3:20])[N:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 14232N,O-DimethylhydroxylamineHCID 58055090HCID 58055090, compound2×

Product 1

HCID 58055072HCID 58055072, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Intermediate 4: 2-(3-(3-fluorobenzyl)ureido)-4-chloromethyl-thiazole (40 g, 0.133 mol), N,O-dimethylhydroxylamine (80 g, 0.820 mol), sodium carbonate (40 g, 0.754 mol), and abs. EtOH (0.2 L) was stirred and heated at 60-70 C for 8-12 hours. The mixture was diluted with water (0.8 L) and cooled to 20 C with continued stirring. The solids were collected by filtration, washed with water, and dried in vacuo to afford the title compound (37 g, 86% yield).

Workup

  1. temperatureheated at 60-70 C for 8-12 hours
  2. temperaturecooled to 20 C with continued stirring
  3. filtrationThe solids were collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-697d9b6e2e63438da23dd743394857bf
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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