Oxalyl chloride → 5-(3-Methoxypropyl)-2-phenylthiazole-4-carbonyl chloride

HRID 453297Notes

Reaction equation

HRID 453297 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][O:8][CH2:9][CH2:10][CH2:11][C:12]1[S:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14]C=1C([O-])=O>C(Cl)Cl.CN(C=O)C>[CH3:7][O:8][CH2:9][CH2:10][CH2:11][C:12]1[S:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][C:1]=1[C:2]([Cl:4])=[O:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 866602305-(3-Methoxypropyl)-2-phenylthiazole-4-carboxylate

Product 1

HCID 585518965-(3-Methoxypropyl)-2-phenylthiazole-4-carbonyl chlorideYield 99.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (67.2 mmol, 5.9 mL) was slowly added to a room temperature solution of 5-(3-methoxypropyl)-2-phenylthiazole-4-carboxylate (22.4 mmol, 6.2 g) in CH2Cl2 (100 mL). 3 drops of DMF were added and the reaction became homogeneous over ˜20 min. The reaction was stirred for 3 h, then concentrated under reduced pressure. The crude product was dissolved in CH2Cl2 (150 mL) and concentrated under reduced pressure. The crude product was dissolved in EtOAc (150 mL), washed with brine (2×100 mL), dried (MgSO4), and concentrated under reduced pressure to give 5-(3-methoxypropyl)-2-phenylthiazole-4-carbonyl chloride as a tan solid (6.6 g, 99% yield).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe crude product was dissolved in CH2Cl2 (150 mL)
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe crude product was dissolved in EtOAc (150 mL)
  5. washwashed with brine (2×100 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b050a8a07e914385bcc5cafeaf25d393
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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