Bromoacetic Acid → HCID 53699943, compound

HRID 34703Notes

Reaction equation

HRID 34703 reaction equation
[Br:1][CH2:2][C:3]([OH:5])=O.[NH2:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:8]=1[OH:21]>C1COCC1>[Br:1][CH2:2][C:3]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:8]=1[OH:21])=[O:5]

Participants

4

Reactant 2

HCID 6227Bromoacetic AcidHCID 141698072-Amino-4-(benzyloxy)phenol

Product 1

HCID 53699943HCID 53699943, compoundYield 505.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bromoacetic acid (13.9 g, 0.01 mole) and dicyclohexyldicarbodiimide (DCCD, 20.6 g, 0.01 mole) were added at room temperature under stirring to the amine ((b), 21.5 g, 0.01 mole) in THF (200 ml). After 1 hour the reaction mixture was filtered and the liquid evaporated to dryness under vacuum. The residue was crystallized from acetic acid (50 ml) to give the bromoamide ((c), 17 g, 50%) as white prisms. The product structure was confirmed by NMR analysis.

Workup

  1. filtrationAfter 1 hour the reaction mixture was filtered
  2. customthe liquid evaporated to dryness under vacuum
  3. customThe residue was crystallized from acetic acid (50 ml)

Sources & evidence

ORD record
ord-526347ab305542db842a0d9114359bdc
Source dataset
uspto-grants-1988_08
Patent number
US04762925

Reaction notes

Loading…