Oxalyl chloride → HCID 86229119, compound

HRID 30287Notes

Reaction equation

HRID 30287 reaction equation
[C:1]1([CH:7]([N:9]2[CH2:13][CH:12]([C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)[CH:11]([C:19]([OH:21])=O)[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:25])=O>ClCCl.CN(C=O)C>[C:1]1([CH:7]([N:9]2[CH2:13][CH:12]([C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)[CH:11]([C:19]([Cl:25])=[O:21])[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 67206550HCID 67206550, compound

Product 1

HCID 86229119HCID 86229119, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The product from step c) (1064 mg, 3.53 mmol) was dissolved in 20 mL of dichloromethane and cooled to 0° C. under N2 atmosphere and oxalyl chloride (1345 mg, 10.59 mmol) was added, followed by 2 drops of DMF. The reaction was stirred at 0° C. for 15 minutes and was allowed to come to room temperature. The reaction mixture was stirred for 1.5 hours and was evaporated to dryness to give the subtitle compound as a solid. MS calculated for C17H18ClNOS+H: 320, observed as methyl ester [dissolved in methanol]+H: 316.

Workup

  1. customto come to room temperature
  2. stirringThe reaction mixture was stirred for 1.5 hours
  3. customwas evaporated to dryness

Sources & evidence

ORD record
ord-86e4200b507844be898358c1562c4fec
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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