Methanol → HCID 20294547, compound

HRID 2082880Notes

Reaction equation

HRID 2082880 reaction equation
[CH2:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([S:20](=[O:23])(=[O:22])[NH2:21])[C:12]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:8]=O)[CH:2]=[CH2:3].[CH:24]([NH2:27])([CH3:26])[CH3:25].CO.[BH4-].[Na+]>O.C(O)(=O)C>[CH2:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([S:20](=[O:23])(=[O:22])[NH2:21])[C:12]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][NH:27][CH:24]([CH3:26])[CH3:25])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 887MethanolHCID 6363IsopropylamineHCID 4311764Sodium borohydrideHCID 202946155-Formyl-2-phenoxy-3-[(prop-2-en-1-yl)amino]benzene-1-sulfonamide

Product 1

HCID 20294547HCID 20294547, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 3-allylamino-4-phenoxy-5-sulfamylbenzaldehyde (10 g; prepared as described in Example 91), isopropylamine (4.0 ml) and methanol (100 ml) is stirred at 22°-25° C. for 24 hours and is then refluxed for 2 hours. To the stirred solution, sodium borohydride (4.0 g) is added in small portions during about 45 minutes, keeping the temperature at 0°-5° C. by external cooling. After the addition is completed, the reaction mixture is stirred at 0°-5° C. for a further 2 hours, whereafter acetic acid (4 ml) followed by water (300 ml) are cautiously added to precipitate crude (3-allylamino-4-phenoxy-5-sulfamylbenzyl)isopropylamine. After filtration and recrystallization from aqueous ethanol it is obtained with a melting point of 98°-100° C. The material (IR, analysis) is identical with the material prepared as in Example 113.

Workup

  1. temperatureis then refluxed for 2 hours
  2. customat 0°-5° C.
  3. additionAfter the addition
  4. additionare cautiously added
  5. customto precipitate crude (3-allylamino-4-phenoxy-5-sulfamylbenzyl)isopropylamine
  6. filtrationAfter filtration and recrystallization from aqueous ethanol it
  7. customis obtained with a melting point of 98°-100° C
  8. customThe material (IR, analysis) is identical with the material prepared as in Example 113

Sources & evidence

ORD record
ord-9117e479a25e4c6ca77a7d731b2638eb
Source dataset
uspto-grants-1978_04
Patent number
US04082851

Reaction notes

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