4-(Bromomethyl)benzoic acid → HCID 43627730, compound

HRID 1485065Notes

Reaction equation

HRID 1485065 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.[ClH:12].CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:36][NH:37][O:38][CH3:39]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:12][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:37]([O:38][CH3:39])[CH3:36])=[O:8])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 225994-(Bromomethyl)benzoic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 43627730HCID 43627730, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 4-(bromomethyl)benzoic acid (10.7 g) in chloroform (200 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (10.5 g), 1-hydroxybenzotriazole monohydrate (8.38 g), N,O-dimethylhydroxylamine hydrochloride (4.85 g), and triethylamine (6.94 mL) were added. After stirring the mixture at room temperature for 53 hours, chloroform (200 mL) was added. The mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, a saturated aqueous solution of ammonium chloride, and saturated brine successively. After passage through a phase separator, the washed mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-40:60) to give 4-(chloromethyl)-N-methoxy-N-methylbenzamide as a colorless oil (3.23 g).

Workup

  1. washThe mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate
  2. concentrationAfter passage through a phase separator, the washed mixture was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-40:60)

Sources & evidence

ORD record
ord-ba39c7f2249b4aad83bf69565a432df3
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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