Acetic Acid → (3-n-Butylamino-4-phenoxy-5-sulfamylbenzyl)-3-hydroxybenzylamine

HRID 1390073Notes

Reaction equation

HRID 1390073 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([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)[CH2:9][NH2:10])[CH2:2][CH2:3][CH3:4].[BH4-].[Na+].[C:27]([OH:30])(=O)[CH3:28].O>CO>[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([S:21](=[O:24])(=[O:23])[NH2:22])[C:13]=1[O:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:9][NH:10][CH2:11][C:8]1[CH:7]=[CH:6][CH:28]=[C:27]([OH:30])[CH:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 540392965-(Aminomethyl)-3-(butylamino)-2-phenoxybenzene-1-sulfonamide

Product 1

HCID 54029537(3-n-Butylamino-4-phenoxy-5-sulfamylbenzyl)-3-hydroxybenzylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-n-butylamino-4-phenoxy-5-sulfamylbenzylamine (1.05 g; prepared as described in Example 289) and m-hydroxybenzaldehyde (0.45 g) in methanol (7 ml) is refluxed for 16 hours. The resulting solution is cooled to 0°-5° C. whereafter sodium borohydride (0.25 g) is added in portions during 5 minutes while stirring. After stirring at 22°-25° C. for a further 3 hours, acetic acid (0.5 ml) followed by water (20 ml) are added to precipitate crude (3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)-3-hydroxybenzylamine. After filtration and recrystallization from ethanol, it is obtained with a melting point of 174°-175° C.

Workup

  1. additionis added in portions during 5 minutes
  2. stirringAfter stirring at 22°-25° C. for a further 3 hours
  3. additionare added
  4. customto precipitate crude (3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)-3-hydroxybenzylamine
  5. filtrationAfter filtration and recrystallization from ethanol
  6. customit is obtained with a melting point of 174°-175° C.

Sources & evidence

ORD record
ord-b16ae998df8f412dbbb24a7f4108edc3
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

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