Acetic Acid → HCID 70573560, compound

HRID 1390081Notes

Reaction equation

HRID 1390081 reaction equation
O.[NH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([S:21](=[O:24])(=[O:23])[NH2:22])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][CH:7]=[CH:8][CH2:9][NH2:10].[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[BH4-].[Na+].C(O)(=O)C>CO.O>[CH2:25]([NH:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([S:21](=[O:24])(=[O:23])[NH2:22])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][CH:7]=[CH:8][CH2:9][NH2:10])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 70574273HCID 70574273, compound

Product 1

HCID 70573560HCID 70573560, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of (3-amino-4-phenoxy-5-sulfamylbenzyl)allylamine hydrate (3.3 g; prepared as described in Example 111) and benzaldehyde (1.2 g) in methanol (35 ml) is refluxed for 16 hours. Sodium borohydride (1.0 g) is then during 30 minutes added in portions while stirring at 0°-5° C. After additional stirring for 2 hours, acetic acid (1.0 ml) followed by water (120 ml) is cautiously added to precipitate crude (3-benzylamino-4-phenoxy-5-sulfamylbenzyl)allylamine. After filtration and recrystallization twice from aqueous ethanol, it is obtained with a melting point of 139°-140° C. The material (IR, analysis) is identical with the material prepared as in Example 150.

Workup

  1. additionduring 30 minutes added in portions
  2. stirringAfter additional stirring for 2 hours
  3. additionis cautiously added
  4. customto precipitate crude (3-benzylamino-4-phenoxy-5-sulfamylbenzyl)allylamine
  5. filtrationAfter filtration and recrystallization twice from aqueous ethanol
  6. customit is obtained with a melting point of 139°-140° C
  7. customThe material (IR, analysis) is identical with the material prepared as in Example 150

Sources & evidence

ORD record
ord-af311fcdb4b44e259d8a2772de1cafb5
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

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