Butyl iodide → HCID 54063712, compound

HRID 1390072Notes

Reaction equation

HRID 1390072 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9]CN)[CH2:2][CH2:3][CH3:4].C(=O)([O-])O.[Na+].[CH2:31](I)[CH2:32][CH2:33][CH3:34].[CH3:36][N:37](C)P(=O)(N(C)C)N(C)C>O>[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][N:37]([CH2:31][CH2:32][CH2:33][CH3:34])[CH3:36])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 10962Butyl iodideHCID 12679Hexamethylphosphoramide2×HCID 516892Sodium BicarbonateHCID 57105491HCID 57105491, compound

Product 1

HCID 54063712HCID 54063712, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of (3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)methylamine (3.6 g; prepared as described in Example 115), sodium hydrogen carbonate (0.9 g) and hexamethylphosphoric triamide (15 ml) a solution of n-butyl iodide (1.85 g) in hexamethylphosphoric triamide (5 ml) is dropwise added during about one hour. After additional stirring for 30 minutes, the mixture is diluted with water to precipitate crude (3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)-n-butylmethylamine. After filtration and recrystallization twice from ethanol it is obtained with a melting point of 103°-104° C. The material (IR, analysis) is identical with the material prepared as in Example 128.

Workup

  1. additionis dropwise added during about one hour
  2. customto precipitate crude (3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)-n-butylmethylamine
  3. filtrationAfter filtration and recrystallization twice from ethanol it
  4. customis obtained with a melting point of 103°-104° C
  5. customThe material (IR, analysis) is identical with the material prepared as in Example 128

Sources & evidence

ORD record
ord-4ce588048bf94970b8b329079ceb8c0d
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

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