Hydrochloric Acid → HCID 67606320, compound

HRID 1626974Notes

Reaction equation

HRID 1626974 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([O:14]C)=[CH:13][C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+].Cl>ClCCl>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=3[N:7]=[N:6]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 686570341-(Cyclopropylmethyl)-5-methoxy-1H-benzotriazole

Product 1

HCID 67606320HCID 67606320, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(Cyclopropylmethyl)-5-methoxy-1H-benzotriazole (Example 5, Step 3; 11.0 g, 54.1 mmol) was dissolved in dichloromethane (200 mL) and cooled to 0° C. The mixture was treated with boron tribromide (108 mL, 1 M dichloromethane solution, 108 mmol, 2 equiv) and warmed to ambient temperature. After stirring for 3 hours, the mixture was treated with sodium bicarbonate over 1 hour (˜100 mL, aqueous saturated) and the mixture was stirred for an additional 14 hours. The mixture was neutralized to pH<5 with 12 N aqueous hydrochloric acid dropwise and the mixture was extracted with dichloromethane containing 10% methanol (4×750 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Workup

  1. temperaturewarmed to ambient temperature
  2. stirringthe mixture was stirred for an additional 14 hours
  3. extractionthe mixture was extracted with dichloromethane containing 10% methanol (4×750 mL)
  4. dry with materialThe combined organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0fbef002151d44f98ba37afaeae5b9a3
Source dataset
uspto-grants-2014_07
Patent number
US08785481B2

Reaction notes

Loading…