Benzyl Bromide → 3-Benzylamino-4-isopropylamino-5-sulphamyl-benzoic acid

HRID 1287794Notes

Reaction equation

HRID 1287794 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:15](=[O:18])(=[O:17])[NH2:16])[C:10]=1[NH:11][CH:12]([CH3:14])[CH3:13])[C:5]([OH:7])=[O:6].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:19]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:15](=[O:18])(=[O:17])[NH2:16])[C:10]=1[NH:11][CH:12]([CH3:13])[CH3:14])[C:5]([OH:7])=[O:6])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 215059903-Amino-4-isopropylamino-5-sulphamyl-benzoic acid

Product 1

HCID 215060283-Benzylamino-4-isopropylamino-5-sulphamyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-amino-4-isopropylamino-5-sulphamyl-benzoic acid (2.62 g), benzyl bromide (4.28 g), and anhydrous ethanol (25 ml) was refluxed for 24 hours. The reaction mixture was evaporated in vacuo. 1N sodium hydroxide (30 ml) was added, and the mixture was heated on a steam bath for 1 hour. After cooling and extracting with diethyl ether, the aqueous layer was adjusted to a pH of 3 by addition of a 4N hydrochloric acid. The precipitated 3-benzylamino-4-isopropylamino-5-sulphamyl-benzoic acid was collected by suction and recrystalized from aqueous ethanol. The melting point was 233°-234° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. addition1N sodium hydroxide (30 ml) was added
  4. temperaturethe mixture was heated on a steam bath for 1 hour
  5. temperatureAfter cooling
  6. extractionextracting with diethyl ether
  7. additionthe aqueous layer was adjusted to a pH of 3 by addition of a 4N hydrochloric acid
  8. customThe precipitated 3-benzylamino-4-isopropylamino-5-sulphamyl-benzoic acid was collected by suction
  9. customrecrystalized from aqueous ethanol

Sources & evidence

ORD record
ord-995f39cef23e4df9a0070e07fc1abe91
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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