Phosphorus oxychloride → HCID 86720282, compound

HRID 1777485Notes

Reaction equation

HRID 1777485 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[S:11][C:12]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH:4]=1.O=P(Cl)(Cl)[Cl:27]>>[Cl:27][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[S:11][C:12]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 57333493HCID 57333493, compound

Product 1

HCID 86720282HCID 86720282, compoundYield 63%

Conditions

Temperature
110 °C

Procedure

(2-((6-(Pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methanol 101 (0.12 g, 0.36 mmol, 1 eq.) was dissolved in POCl3 (3 mL) under N2, and the suspension was stirred at 110° C. for 2 hours. After cooling, POCl3 was evaporated under reduced pressure and the residue was basified with sat. Na2CO3 solution, then extracted with DCM, dried and concentrated in vacuo to afford N-(4-(chloromethyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine (80 mg, 63%) which was used directly in the next step.

Workup

  1. temperatureAfter cooling
  2. customPOCl3 was evaporated under reduced pressure
  3. extractionextracted with DCM
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7589414610d41d9bdcf80154fb42d11
Source dataset
uspto-grants-2016_02
Patent number
US09266874B2

Reaction notes

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