Thionyl Chloride → HCID 86614199, compound

HRID 1671808Notes

Reaction equation

HRID 1671808 reaction equation
[CH:1]([NH:4][C:5]1[S:6][C:7]2[C:12]([N:13]=1)=[CH:11][CH:10]=[C:9]([CH2:14]O)[N:8]=2)([CH3:3])[CH3:2].O=S(Cl)[Cl:18]>C(Cl)Cl>[ClH:18].[ClH:18].[Cl:18][CH2:14][C:9]1[N:8]=[C:7]2[S:6][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:13][C:12]2=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57527200HCID 57527200, compound

Product 1

HCID 86614199HCID 86614199, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-(isopropylamino)thiazolo[5,4-b]pyridin-5-yl)methanol (0.71 g, 3.18 mmol, 1.0 eq.) in CH2Cl2 (11 mL) under nitrogen at 0° C. was added SOCl2 (1.0 mL, 13.7 mmol, 4.3 eq.). After 5 min., the cold bath was removed, and the reaction mixture was stirred to room temperature for 10 min. and then refluxed for 2.75 hr. After cooling to room temperature, the reaction mixture was concentrated in vacuo to give 5-(chloromethyl)-N-isopropylthiazolo[5,4-b]pyridin-2-amine dihydrochloride as a white solid (0.90 g, 90% yield).

Workup

  1. customthe cold bath was removed
  2. temperaturerefluxed for 2.75 hr
  3. temperatureAfter cooling to room temperature
  4. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d7336cab2d4944e0857e2781d90aff13
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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