Acetic Acid → HCID 86687561, compound

HRID 1473506Notes

Reaction equation

HRID 1473506 reaction equation
C(S[C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=3[O:29][CH3:30])=[CH:14][CH:15]=[N:16]2)=[CH:11][N:10]=1)C1C=CC=CC=1.C(Cl)Cl.C(O)(=O)C.[S:38]([Cl:42])(Cl)(=[O:40])=[O:39]>O>[CH3:30][O:29][C:20]1[CH:21]=[C:22]([C:25]([F:28])([F:26])[F:27])[CH:23]=[CH:24][C:19]=1[C:13]1[C:12]2[C:17](=[CH:18][C:9]([S:38]([Cl:42])(=[O:40])=[O:39])=[N:10][CH:11]=2)[N:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 86687560HCID 86687560, compound

Product 1

HCID 86687561HCID 86687561, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A round bottomed flask cooled to 0° C., was charged with 7-(benzylthio)-4-(2-methoxy-4-(trifluoromethyl)phenyl)-1,6-naphthyridine (0.129 g, 0.302 mmol), DCM (2.88 ml), acetic acid (0.072 ml), and water (0.072 ml). After stirring for 5 minutes at 0° C., sulfuryl chloride (0.025 ml, 0.302 mmol) was added and stirring was continued for an additional 1 hour at 0° C. The reaction was concentrated, dissolved in minimal DCM and purified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane) to afford 0.093 g of 4-(2-methoxy-4-(trifluoromethyl)phenyl)-1,6-naphthyridine-7-sulfonyl chloride as an off white solid. m/z (ESI) 402.9 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued for an additional 1 hour at 0° C
  3. concentrationThe reaction was concentrated
  4. dissolutiondissolved in minimal DCM
  5. custompurified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane)

Sources & evidence

ORD record
ord-63a4605ece394e6594b3465e1f966f51
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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