Sodium Carbonate → HCID 72334044, compound

HRID 1963001Notes

Reaction equation

HRID 1963001 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][O:11][C:12]3[C:13]([F:21])=[C:14]([C:19]#[N:20])[C:15]([F:18])=[CH:16][CH:17]=3)=[N:7][C:6]=2[CH:22]=1.C([O-])([O-])=O.[Na+].[Na+].Cl.[NH2:30][OH:31]>CCO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][O:11][C:12]3[C:13]([F:21])=[C:14]([C:19](=[N:30][OH:31])[NH2:20])[C:15]([F:18])=[CH:16][CH:17]=3)=[N:7][C:6]=2[CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium Carbonate2×HCID 443297Hydroxyamine hydrochloride2×HCID 59591441HCID 59591441, compound

Product 1

HCID 72334044HCID 72334044, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-[(5-chloro-1,3-benzothiazol-2-yl)methoxy]-2,6-difluorobenzene-carbonitrile (250 mg, 0.74 mmol, 1 equiv.), Na2CO3 (181 mg, 1.70 mmol, 2.3 equiv.) and hydroxylamine hydrochloride (103 mg, 1.48 mmol, 2 equiv.) in absolute EtOH (5 ml) was stirred at 70° C. for 8 h. Excess Na2CO3 (181 mg, 1.70 mmol, 2.3 equiv.) and hydroxylamine hydrochloride (103 mg, 1.48 mmol, 2 equiv.) were added and the heating continued for 1 h. The reaction mixture cooled at room temperature, diluted with water (40 ml) and extracted with CH2Cl2 (3×60 ml). The combined organic extracts were dried (MgSO4) and evaporated to dryness under reduced pressure, to give 201 mg (73% yield) of the desired product. Mp 169-170° C., HPLC (Gemini C18, 50×4.6 mm): m/z 370 [M+H]+, Rt=3.82 min.

Workup

  1. waitthe heating continued for 1 h
  2. temperatureThe reaction mixture cooled at room temperature
  3. extractionextracted with CH2Cl2 (3×60 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8e5891d37c814a9390982726c2a6545c
Source dataset
uspto-grants-2013_04
Patent number
US08415383B2

Reaction notes

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