Dimethylformamide → HCID 21643578, compound

HRID 2174184Notes

Reaction equation

HRID 2174184 reaction equation
CN([CH:4]=[O:5])C.P(Cl)(Cl)([Cl:8])=O.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[S:18][CH:19]=[C:20](O)[N:21]=2)[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>>[Cl:8][C:20]1[N:21]=[C:17]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[S:18][C:19]=1[CH:4]=[O:5]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 21643569HCID 21643569, compound

Product 1

HCID 21643578HCID 21643578, compound

Conditions

Temperature
110 °C

Procedure

Dry DMF (20 ml, 0.255 mol) was cooled to 0-5° C. with an ice/water bath. Phosphorus oxychloride (20 ml, 0.215 mol) was added dropwise over 0.5 h. 2-(3-pyridyl)thiazol-4-ol (hybromide salt, 13 g, 0.05 mol) was added in one portion and the reaction mixture was heated to 110° C. for 15 min. After cooling the reaction mixture was poured on ice water and neutralized with solid potassium carbonate. The precipitate was filtered, washed with water, once with ethanol, and dried to dryness to get 4-chloro-2-(3-pyridyl)thiazole-5-carbaldehyde as brown solid. 1H NMR (300 Mz, DMSO-d6): δ: 10.00 (s, 1H), 9.21 (d, 1H, J=1.2 Hz), 8.78 (dd, 1H, J=1.5 Hz), 8.42 (d, 1H, J=7.2 Hz), 7.60 (m, 1H). MS(ESI): 255, 257 (M+MeOH).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationThe precipitate was filtered
  3. washwashed with water, once with ethanol
  4. customdried to dryness

Sources & evidence

ORD record
ord-458bacdb338643aba05a43c3a3a9a1f2
Source dataset
uspto-grants-2015_06
Patent number
US09060519B2

Reaction notes

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