Diethyl Ether → HCID 18953868, compound

HRID 2379877Notes

Reaction equation

HRID 2379877 reaction equation
[NH2:1][C:2](=[N:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16]O)[N:11]=2)[N:9]=1)[NH2:3].S(Cl)([Cl:20])=O.C(OCC)C>ClCCl.O1CCCC1>[Cl:20][CH2:16][C:12]1[N:11]=[C:10]([C:8]2[N:9]=[C:5]([N:4]=[C:2]([NH2:3])[NH2:1])[S:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 18953921HCID 18953921, compound

Product 1

HCID 18953868HCID 18953868, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(diaminomethyleneamino)-4-(6-hydroxymethylpyridin-2-yl)thiazole (1.0 g) and thionyl chloride (10 ml) in a mixture of dichloromethane (10 ml) and tetrahydrofuran (10 ml) was stirred for 70 hours at ambient temperature. To the reaction mixture was added a diethyl ether (30 ml) and isolated precipitate was collected by filtration. The precipitate was added to a mixture of tetrahydrofuran, ethyl acetate and water and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated to give 4-(6-chloromethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (0.97 g).

Workup

  1. customisolated precipitate
  2. filtrationwas collected by filtration
  3. additionThe precipitate was added to a mixture of tetrahydrofuran, ethyl acetate and water
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-dc9eb723d9d44748b3d9e84f30ad67e0
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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