Benzocaine → HCID 23468277, compound

HRID 443653Notes

Reaction equation

HRID 443653 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14]Br)=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1.CN(C)P(N(C)C)(N(C)C)=O>O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 23468299HCID 23468299, compound

Product 1

HCID 23468277HCID 23468277, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The solution of 7.0 g. of 2-(4-bromo-1-naphthyloxy)ethyl bromide and 7.9 g. of ethyl 4-aminobenzoate in 50 ml. of hexamethylphosphoramide is heated for 18 hours, then cooled and diluted with 50 ml. of water. The precipitate is collected and crystallized from 200 ml. of methylcyclohexane and then from 100 ml. of ethanol, m.p. 126°-127° C.

Workup

  1. temperaturecooled
  2. additiondiluted with 50 ml
  3. customThe precipitate is collected
  4. customcrystallized from 200 ml

Sources & evidence

ORD record
ord-e5f5bf07302d437f9c5c6454e5170c1f
Source dataset
uspto-grants-1981_04
Patent number
US04260816

Reaction notes

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