Dimethylformamide → Thiane-4-carbonyl chloride

HRID 460681Notes

Reaction equation

HRID 460681 reaction equation
[S:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=O)[CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:13])=O.CN(C)C=O>ClCCl>[S:1]1[CH2:6][CH2:5][CH:4]([C:7]([Cl:13])=[O:9])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 21598642Tetrahydrothiopyran-4-carboxylic acid

Product 1

HCID 14547368Thiane-4-carbonyl chlorideYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cold solution of 1.36 g (9.32 mmol) tetrahydro-thiopyran-4-carboxylic acid in 25 mL of dichloromethane (DCAM) was added dropwise 1.1 mL (12.6 mmol) of oxalyl chloride, and the resulting mixture was stirred at 0° C. for 2 h. Then 2 μL of dimethylformamide (DMF cat) was added, and the reaction mixture was stirred at rt for 2 h, and concentrated to give 1.43 g (93%) of desired tetrahydro-thiopyran-4-carbonyl chloride as a brown oil as indicated by 1H NMR. The product was used with out any further purification in the next step toward the preparation of 6-(4-Benzyloxy-phenyl)-7-(tetrahydro-thiopyran-4-yl)-3-(1H-tetrazol-5-yl)-pyrazolo[1,5-a]pyrimidine (below, entry 375).

Workup

  1. stirringthe reaction mixture was stirred at rt for 2 h
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-06f31934d62d4799a9f72039080f560c
Source dataset
uspto-grants-2007_03
Patent number
US07196111B2

Reaction notes

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