Benzyl Bromide → HCID 21520110, compound

HRID 1605517Notes

Reaction equation

HRID 1605517 reaction equation
[NH2:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[C:4]([SH:11])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(=O)([O-])O.[Na+]>[NH2:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[C:4]([S:11][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 21520063HCID 21520063, compound

Product 1

HCID 21520110HCID 21520110, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

5-Amino-4-(p-methoxyphenoxy)-3-mercaptobenzoic acid (2 g) is dissolved in 1 N sodium hydrogen carbonate (50 ml), and after addition of benzyl bromide (0.85 ml), the reaction mixture is stirred for 17 hours. After extraction twice with diethyl ether (25 ml), the aqueous layer is adjusted to pH 2 by addition of 4 N hydrochloric acid. The precipitated 5-amino-3-benzylthio-4-(p-methoxyphenoxy)-benzoic acid is collected and recrystallized from aqueous ethanol. After drying in vacuo at 80° C, the compound is obtained with a melting point of 158°-161° C.

Workup

  1. extractionAfter extraction twice with diethyl ether (25 ml)
  2. additionthe aqueous layer is adjusted to pH 2 by addition of 4 N hydrochloric acid
  3. customThe precipitated 5-amino-3-benzylthio-4-(p-methoxyphenoxy)-benzoic acid is collected
  4. customrecrystallized from aqueous ethanol
  5. customAfter drying in vacuo at 80° C
  6. customthe compound is obtained with a melting point of 158°-161° C.

Sources & evidence

ORD record
ord-49117383166e4cebaa790247bdbb7690
Source dataset
uspto-grants-1976_04
Patent number
US03950376

Reaction notes

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