Triethylamine → HCID 18771469, compound

HRID 1387638Notes

Reaction equation

HRID 1387638 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([S:14]([NH:17][C:18]2[CH:25]=[CH:24][C:21]([CH2:22][OH:23])=[CH:20][CH:19]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1.C(N(CC)CC)C>C(Cl)Cl.CS(C)=O>[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([S:14]([NH:17][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=2)(=[O:15])=[O:16])[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 54090576HCID 54090576, compound

Product 1

HCID 18771469HCID 18771469, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (1.06 mL, 12.1 mmol) in CH2Cl2 (20 mL) was added DMSO (1.8 mL, 25.4 mmol.) at −60° C. and the mixture was stirred for 25 min. A solution of 4-(4-methyl piperazinyl)sulfonamido benzyl alcohol (3.0 g, 10.5 mmol) in CH2Cl2 (25 mL) and DMSO (5 mL) was added and the mixture was stirred for 1.5 h at −60° C. Triethylamine (7.4 mL) was added and the mixture was partitioned between brine and EtOAc. The organic extract was concentrated, then purified by flash chromatography to yield the title compound (1.0 g, 33%).

Workup

  1. stirringthe mixture was stirred for 1.5 h at −60° C
  2. customthe mixture was partitioned between brine and EtOAc
  3. extractionThe organic extract
  4. concentrationwas concentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-b3b9b22a93604b6e81ff52e8ebf76ef3
Source dataset
uspto-grants-2001_07
Patent number
US06268370B1

Reaction notes

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