Hydrochloric Acid → HCID 70976689, compound

HRID 1851709Notes

Reaction equation

HRID 1851709 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[S:8][C:7]2=[N:9][C:10]([C:12]([F:15])([F:14])[F:13])=[CH:11][N:6]2[N:5]=1.[CH2:16]=[O:17].Cl.O>S1(CCCC1)(=O)=O>[CH3:1][O:2][CH2:3][C:4]1[S:8][C:7]2=[N:9][C:10]([C:12]([F:15])([F:13])[F:14])=[C:11]([CH2:16][OH:17])[N:6]2[N:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 962WaterHCID 67117085Imidazo (2,1-b)-1,3,4-thiadiazole, 2-(methoxymethyl)-6-(trifluoromethyl)-

Product 1

HCID 70976689HCID 70976689, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
110 °C

Procedure

2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole a2 (10 g, 42.16 mmol, 1 eq), formaldehyde (16 g, 421.6 mmol, 10 eq) and hydrochloric acid (37%, 8.2 ml, 2 eq) are diluted in sulfolane (250 ml). The reaction mixture is heated at 110° C. overnight. Water (500 ml) is added and the mixture is heated at 50° C. for 2 h. The solvent is then removed under reduced pressure. The residue is purified by chromatography over silicagel (gradient; eluent: CH2Cl2/MeOH/NH4OH from 100/0/0 to 99/1/0.1) to afford 6.5 g of [2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methanol a3 as a yellow solid.

Workup

  1. temperaturethe mixture is heated at 50° C. for 2 h
  2. customThe solvent is then removed under reduced pressure
  3. customThe residue is purified by chromatography over silicagel (gradient; eluent: CH2Cl2/MeOH/NH4OH from 100/0/0 to 99/1/0.1)

Sources & evidence

ORD record
ord-2b7c183b80ba441c955ddcffa5020942
Source dataset
uspto-grants-2015_02
Patent number
US08957218B2

Reaction notes

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