Bromoacetic Acid → HCID 53699943, compound

HRID 280827Notes

Reaction equation

HRID 280827 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 50%

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 strusture 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-fa7bd977ae3a41218e41f2de36b42189
Source dataset
uspto-grants-1986_05
Patent number
US04591548

Reaction notes

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