Water → 5-(Aminomethyl)-3-(butylamino)-2-phenoxybenzene-1-sulfonamide

HRID 1390068Notes

Reaction equation

HRID 1390068 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([S:27](=[O:30])(=[O:29])[NH2:28])[C:19]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]#[N:16])[CH2:8][CH2:9][CH3:10].C(OCC)(=O)C.O>COCCOC>[CH2:7]([NH:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([S:27](=[O:30])(=[O:29])[NH2:28])[C:19]=1[O:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:15][NH2:16])[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 538981403-(Butylamino)-5-cyano-2-phenoxybenzene-1-sulfonamide

Product 1

HCID 540392965-(Aminomethyl)-3-(butylamino)-2-phenoxybenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirred mixture of lithium aluminium hydride (5.0 g) and 1,2-dimethoxyethane (100 ml) a solution of 3-n-butylamino-4-phenoxy-5-sulfamylbenzonitrile (15 g) in dry 1,2-dimethoxyethane (150 ml) is during about one hour at 100° C. dropwise added, and the mixture is stirred and refluxed for a further 16 hours. After cooling, ethyl acetate (10 ml) followed by water (20 ml) are very cautiously added dropwise, whereafter the mixture is stirred for a further 30 minutes. It is then heated on a steam-bath and filtered hot; the filter-cake is carefully washed with hot 2-methoxyethanol (3 portions of 50 ml). The combined filtrates are evaporated in vacuo to yield crude 3-n-butylamino-4-phenoxy-5-sulfamylbenzylamine. After recrystallization from 2-methoxyethanol it is obtained with a melting point of 197°-198° C. The material (IR, analysis) is identical with the material prepared as in Example 289.

Workup

  1. additiondropwise added
  2. temperaturerefluxed for a further 16 hours
  3. temperatureAfter cooling
  4. additionare very cautiously added dropwise, whereafter the mixture
  5. stirringis stirred for a further 30 minutes
  6. temperatureIt is then heated on a steam-bath
  7. filtrationfiltered hot
  8. washthe filter-cake is carefully washed with hot 2-methoxyethanol (3 portions of 50 ml)
  9. customThe combined filtrates are evaporated in vacuo

Sources & evidence

ORD record
ord-2a0a87531fb54e308a817f5b00d3aa45
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

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