Chloroacetaldehyde → HCID 25261014, compound

HRID 1966207Notes

Reaction equation

HRID 1966207 reaction equation
[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]([NH2:17])=[S:16])=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:19][CH:20]=O>CN(C=O)C>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[S:16][CH:19]=[CH:20][N:17]=2)=[N:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 86644601HCID 86644601, compound

Product 1

HCID 25261014HCID 25261014, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

8.4 (5-Phenoxy-pyridine-2-yl)-thiourea (0.3 mmol) is dissolved in DMF (1 ml) and chloro-acetaldehyde (1.1 eq., 55% in water) is added and stirred 2 h at 70° C. After cooling to RT the precipitate is filtered, washed with water and dried 16 h in vacuo at 40° C. (5-Phenoxy-pyridine-2-yl)thiazole-2-yl-amine is obtained as colourless powder in a yield of 66%; mp. 161.4-162.4° C.; HPLC (method C): 1.69 min; LC-MS (method A): 1.559 min, 270.15 (M+H+); 1H-NMR (DMSO-d6, 500 MHz): δ [ppm] 11.248 (s, 1H), 8.114 (d, 1H, J=2.7 Hz), 7.523 (dd, 1H, J=9.0 Hz, J=2.7 Hz), 7.387-7.355 (m, 3H), 7.151 (d, 1H, J=9.0 Hz), 7.107 (t, 1H, J=7.1 Hz), 6.997-6.967 (m, 3H).

Workup

  1. temperatureAfter cooling to RT the precipitate
  2. filtrationis filtered
  3. washwashed with water
  4. dry with materialdried 16 h in vacuo at 40° C. (5-Phenoxy-pyridine-2-yl)thiazole-2-yl-amine
  5. customis obtained as colourless powder in a yield of 66%
  6. custom1.69 min
  7. custom1.559 min, 270.15 (M+H+)

Sources & evidence

ORD record
ord-a25eacf0a4034ce29bd490f16fe0b4bd
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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