Dimethylformamide → HCID 22324122, compound

HRID 1430589Notes

Reaction equation

HRID 1430589 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([C:7](O)=[O:8])[N:6]=1.CN(C=O)C.C(Cl)(=O)C([Cl:24])=O>C(Cl)Cl>[CH3:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([C:7]([Cl:24])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 9435352-methyl-5-phenyl-1,3-thiazole-4-carboxylic Acid

Product 1

HCID 22324122HCID 22324122, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-methyl-5-phenyl-1,3-thiazole-4-carboxylic acid (1.47 g, 6.70 mmol) in CH2Cl2 (30 mL) cooled at 0° C. was added DMF (26 μL, 0.34 mmol) and oxalyl chloride (0.73 mL, 8.38 mmol). The reaction was allowed to warm to ambient temperature and stirred for 4 h. The solution was concentrated in vacuo to provide 2-methyl-5-phenyl-1,3-thiazole-4-carbonyl chloride as a yellow-orange oil which gave a mass ion (ES+) of 236.3. 1H NMR δ (ppm) (CDCl3): 7.42-7.46 (5H, m), 2.78 (3H, s).

Workup

  1. temperatureto warm to ambient temperature
  2. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-46cde135028147d086ec62cb4565342d
Source dataset
uspto-grants-2015_01
Patent number
US08940898B2

Reaction notes

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