Water → HCID 178527121, compound

HRID 330518Notes

Reaction equation

HRID 330518 reaction equation
[OH:1][N:2]=[C:3]([NH2:16])[CH2:4][C:5]1[C:14]2[C:9](=[C:10](Cl)[CH:11]=[CH:12]C=2)[CH:8]=[CH:7][CH:6]=1.N1C=CC=CC=1.[S:23](Cl)(Cl)=[O:24].O.[CH2:28]([Cl:30])Cl>>[Cl:30][C:28]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:8]=1[CH:7]=[CH:6][C:5]([CH2:4][C:3]1[NH:16][S:23](=[O:24])[O:1][N:2]=1)=[CH:14]2

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 54400138HCID 54400138, compound

Product 1

HCID 178527121HCID 178527121, compoundYield 16%

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred suspension of N'-hydroxy-2-(5-chloronaphthalenyl)ethanimidamide (470 mg, 2.00 mmol) in CH2Cl2 (3 mL) and pyridine (325 μL, 4.00 mmol) was added thionyl chloride (160 μL, 2.20 mmol) over 2 minutes. The resulting solution was stirred for 25 minutes. H2O (10 mL) was added and the mixture was extracted with CH2Cl2 (2×25 mL). The combined extracts were dried (MgSO4) and concentrated. Purification by flash chromatography (eluant EtOAc/hexane (20:80)) and recrystallization from ethanol/ether gave off-white needles (88 mg, 16%), m.p. 164°-165° C.

Workup

  1. stirringThe resulting solution was stirred for 25 minutes
  2. extractionthe mixture was extracted with CH2Cl2 (2×25 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customPurification
  6. customby flash chromatography (eluant EtOAc/hexane (20:80)) and recrystallization from ethanol/ether

Sources & evidence

ORD record
ord-bb186110b6d8499f9794559e05712d39
Source dataset
uspto-grants-1990_01
Patent number
US04897405

Reaction notes

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