Butyryl chloride → HCID 54096992, compound

HRID 2082902Notes

Reaction equation

HRID 2082902 reaction equation
O.Cl.Cl.[NH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][N:9]([CH3:11])[CH3:10].N[C:27]1[CH:28]=C(C=[C:35](S(=O)(=O)N)[C:36]=1CC1C=CC=CC=1)CN(C)C.Cl.Cl.[OH-].[Na+].CCCC(Cl)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(Cl)Cl.COCCOC.O.C(OCC)(=O)C>[CH2:15]([C:14]1[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:12][C:7]([CH2:8][N:9]([CH3:10])[CH3:11])=[CH:6][C:5]=1[NH:4][CH2:28][CH2:27][CH2:36][CH3:35])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

9

Reactant 4

HCID 8855Butyryl chlorideHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 70574148HCID 70574148, compound

Product 1

HCID 54096992HCID 54096992, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 80711,2-DimethoxyethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a vigorously stirred mixture of (3-amino-4-benzyl-5-sulfamylbenzyl)dimethylamine dihydrochloride hemihydrate (4.0 g; prepared as described in Example 209), 2 N sodium hydroxide (60 ml) and methylene chloride (40 ml) a solution of n-butyryl chloride (1.1 g) in methylene chloride (12 ml) is dropwise added during 30 minutes keeping the temperature at 0°-5° C. by external cooling. After additional stirring at 22°-25° C. for 2 hours, the organic layer is separated, washed with water and dried in the presence of magnesium sulphate. The methylene chloride is then removed in vacuo to yield crude (4-benzyl-3-n-butyrylamido-5-sulfamylbenzyl)-dimethylamine as an oil. The crude amine is dissolved in dry 1,2-dimethoxyethane (50 ml) and the resulting solution is dropwise added at 100° C. during 45 minutes to a stirred mixture of lithium aluminium hydride (2.0 g) and 1,2-dimethoxyethane (40 ml). After additional refluxing and stirring for 16 hours, the mixture is cooled, and ethyl acetate (4 ml) followed by water (8 ml) are very cautiously added. The mixture is stirred for a further 30 minutes and is then heated on a steam-bath and filtered hot. The filtercake is carefully washed with hot 1,2-dimethoxyethane (3 portions of 25 ml), whereafter the combined filtrates are evaporated in vacuo to yield crude (4-benzyl-3-n-butylamino-5-sulfamylbenzyl)dimethylamine. After recrystallization from ethanol it is obtained with a melting point of 111°-113° C. The material (IR, analysis) is identical with the material prepared as in Example 172.

Workup

  1. additionis dropwise added during 30 minutes
  2. customat 0°-5° C.
  3. customthe organic layer is separated
  4. washwashed with water
  5. dry with materialdried in the presence of magnesium sulphate
  6. customThe methylene chloride is then removed in vacuo
  7. customto yield crude (4-benzyl-3-n-butyrylamido-5-sulfamylbenzyl)-dimethylamine as an oil
  8. temperatureAfter additional refluxing
  9. stirringstirring for 16 hours
  10. temperaturethe mixture is cooled
  11. additionare very cautiously added
  12. stirringThe mixture is stirred for a further 30 minutes
  13. temperatureis then heated on a steam-bath
  14. filtrationfiltered hot
  15. washThe filtercake is carefully washed with hot 1,2-dimethoxyethane (3 portions of 25 ml), whereafter the combined filtrates
  16. customare evaporated in vacuo

Sources & evidence

ORD record
ord-a2d4e1e3386f4d5e85279e3cf51381a2
Source dataset
uspto-grants-1978_04
Patent number
US04082851

Reaction notes

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