Butyl iodide → HCID 54063712, compound

HRID 2082894Notes

Reaction equation

HRID 2082894 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 (15ml) a solution of n-butyl iodide (1.85 g) in hexamethylphosphoric triamide (5 ml) is dropwise added during about 1 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 1 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-de3db18c212b4df586934f7082bbbeab
Source dataset
uspto-grants-1978_04
Patent number
US04082851

Reaction notes

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