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

HRID 2082881Notes

Reaction equation

HRID 2082881 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH2:12]([NH:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([S:33](=[O:36])(=[O:35])[NH2:34])[C:25]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:20]([NH2:22])=O)[CH2:13][CH2:14][CH3:15].C(OCC)(=O)C>N1C=CC=CC=1.O>[CH2:12]([NH:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([S:33](=[O:36])(=[O:35])[NH2:34])[C:25]=1[O:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:20][NH2:22])[CH2:13][CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 215060653-Butylamino-4-phenoxy-5-sulphamyl-benzamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a mixture of lithium aluminium hydride (1.6 g) and dry tetrahydrofuran (10 ml), a solution of 3-n-butylamino-4-phenoxy-5-sulfamylbenzamide (2.25 g) in dry pyridine (20 ml) is added, and the mixture is refluxed for 16 hours. After cooling, ethyl acetate (1 ml) followed by water (6 ml) are very cautiously added dropwise, whereafter the mixture is stirred for a further 30 minutes. It is then heated on a steambath and filtered hot; the filter-cake is carefully washed with hot 2-methoxyethanol (3 portions of 20 ml). The combined filtrates are evaporated in vacuo and the residue is crystallized from ethanol to give 3-n-butylamino-4-phenoxy-5-sulfamylbenzylamine with a melting point of 195°-198° C.

Workup

  1. temperaturethe mixture is refluxed for 16 hours
  2. temperatureAfter cooling
  3. additionare very cautiously added dropwise, whereafter the mixture
  4. temperatureIt is then heated on a steambath
  5. filtrationfiltered hot
  6. washthe filter-cake is carefully washed with hot 2-methoxyethanol (3 portions of 20 ml)
  7. customThe combined filtrates are evaporated in vacuo
  8. customthe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-db1663a0d12b42b286a9624187245c7b
Source dataset
uspto-grants-1978_04
Patent number
US04082851

Reaction notes

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