Carbon tetrabromide → HCID 57850288, compound

HRID 736668Notes

Reaction equation

HRID 736668 reaction equation
[CH:1]1([CH:4]([NH:8][C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6]O)[CH2:3][CH2:2]1.C(Br)(Br)(Br)[Br:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:16][CH2:6][CH2:5][CH:4]([NH:8][C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH:1]1[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68520514HCID 68520514, compound

Product 1

HCID 57850288HCID 57850288, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

The 1-(1-cyclopropyl-3-hydroxy-propyl)-3-isopropyl-urea (0.189 g, 0.950 mmol) was then dissolved in CH2Cl2 (10 mL) and CBr4 (0.477 g, 1.40 mmol) was added and the mixture was cooled to 0° C. To the mixture was added PPh3-polymer-bound resin (0.889 g, 1.40 mmol; 1.6 mmol/g) in portionwise. After stirring for at rt for 3 h, the mixture was diluted with CH2Cl2 (50 mL), filtered, and washed with CH2Cl2/MeOH/Acetone. The combined filtrates were concentrated in vacuo to give 1-(3-Bromo-1-cyclopropyl-propyl)-3-isopropyl-urea (0.212 g). GC-MS m/z 262.

Workup

  1. filtrationfiltered
  2. washwashed with CH2Cl2/MeOH/Acetone
  3. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-6ef820c607e147d5a75994eeb008593c
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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