Methanol → HCID 22283108, compound

HRID 2250798Notes

Reaction equation

HRID 2250798 reaction equation
C([O:8][C:9]1[C:14]2[N:15]=[C:16]([NH:18][C:19](=[O:28])[C:20]3[CH:25]=[CH:24][C:23]([CH2:26][Cl:27])=[CH:22][CH:21]=3)[S:17][C:13]=2[C:12]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.O.CO>C(Cl)Cl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:27][CH2:26][C:23]1[CH:22]=[CH:21][C:20]([C:19]([NH:18][C:16]2[S:17][C:13]3[C:12]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[CH:11][CH:10]=[C:9]([OH:8])[C:14]=3[N:15]=2)=[O:28])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25135Boron TrichlorideHCID 22283231HCID 22283231, compound

Product 1

HCID 22283108HCID 22283108, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

N-(4-Benzyloxy-7-morpholin-4-yl-benzothiazol-2-yl)-4-chloromethyl-benzamide (1.0 g, 2.0 mmol) were dissolved in CH2Cl2 (10 ml) and treated at −78° C. with tetrabutyl ammonium iodide (0.95 g, 2.6 mmol) and a solution of boron trichloride in CH2Cl2 (1M, 7.4 ml). After subsequent warming to 0° and stirring for additional 2 h, ice (2 g) and then water (10 ml) and methanol (2 ml) were added and the phases separated. The aqueous phases were extracted twice with CH2Cl2/MeOH, the combined organic layers were dried with Na2SO4 and evaporated to dryness. Recrystallization from CH2Cl2/MeOH afforded the title compound as an off-white solid (18%). MS: m/e=403 ([M−H+]−).

Workup

  1. temperatureAfter subsequent warming to 0°
  2. customthe phases separated
  3. extractionThe aqueous phases were extracted twice with CH2Cl2/MeOH
  4. dry with materialthe combined organic layers were dried with Na2SO4
  5. customevaporated to dryness
  6. customRecrystallization from CH2Cl2/MeOH

Sources & evidence

ORD record
ord-fc4b16a44be544d09f6aeda689adc3df
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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