Hydrochloric Acid → (4-Benzyl-3-n-butoxy-5-sulfamylbenzyl)dimethylamine

HRID 2082901Notes

Reaction equation

HRID 2082901 reaction equation
N[C:2]1[C:3]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:4]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]=[C:6]([CH:11]=1)[CH2:7][N:8]([CH3:10])[CH3:9].Cl.[N:25]([O-])=O.[Na+].[S:29](=[O:31])=[O:30]>O.C(O)(=O)C>[CH2:17]([C:3]1[C:2]([S:29](=[O:31])(=[O:30])[NH2:25])=[CH:11][C:6]([CH2:7][N:8]([CH3:10])[CH3:9])=[CH:5][C:4]=1[O:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 20294557(5-Amino-4-benzyl-3-n-butoxybenzyl)dimethylamineHCID 23668193Sodium Nitrite

Product 1

HCID 54147820(4-Benzyl-3-n-butoxy-5-sulfamylbenzyl)dimethylamine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (5-amino-4-benzyl-3-n-butoxybenzyl)dimethylamine (6.25 g) in a mixture of concentrated hydrochloric acid (10 ml) and acetic acid (10 ml) a solution of sodium nitrite (1.4 g) in water (5 ml) is dropwise added during 30 minutes, keeping the temperature at 0°-3° C. by external cooling. After additional stirring at 0° C. for 10 minutes, the resulting diazonium-solution is slowly added to a solution of cupric chloride dihydrate (1.5 g) in water (4 ml) and acetic acid (25 ml) saturated with dry sulphur dioxide while stirring at 22°-25° C. After stirring for a further 1 hour, the mixture is cooled to precipitate crude (4-benzyl-3-n-butoxy-5-chlorosulfonylbenzyl)dimethylamine hydrochloride. The hydrochloride is collected by filtration and washed with a minor amount of ice-cold acetic acid. It is then added in portions to a stirred, saturated solution of dry ammonia in methanol (30 ml) keeping the temperature at 10°-12° C. by external cooling. The resulting solution is stirred for 16 hours at 22°-25° C. and is then diluted with water (100 ml) to precipitate crude (4-benzyl-3-n-butoxy-5-sulfamylbenzyl)dimethylamine. After filtration and recrystallization twice from aqueous ethanol it is obtained with a melting point of 109°-111° C. The material (IR, analysis) is identical with the material prepared as in Example 180.

Workup

  1. additionis dropwise added during 30 minutes
  2. customat 0°-3° C.
  3. stirringwhile stirring at 22°-25° C
  4. stirringAfter stirring for a further 1 hour
  5. temperaturethe mixture is cooled
  6. customto precipitate crude (4-benzyl-3-n-butoxy-5-chlorosulfonylbenzyl)dimethylamine hydrochloride
  7. filtrationThe hydrochloride is collected by filtration
  8. washwashed with a minor amount of ice-cold acetic acid
  9. additionIt is then added in portions to a stirred, saturated solution of dry ammonia in methanol (30 ml)
  10. customat 10°-12° C.
  11. stirringThe resulting solution is stirred for 16 hours at 22°-25° C.
  12. additionis then diluted with water (100 ml)
  13. customto precipitate crude (4-benzyl-3-n-butoxy-5-sulfamylbenzyl)dimethylamine
  14. filtrationAfter filtration and recrystallization twice from aqueous ethanol it
  15. customis obtained with a melting point of 109°-111° C
  16. customThe material (IR, analysis) is identical with the material prepared as in Example 180

Sources & evidence

ORD record
ord-e4731edfce434268999bfb589674ac1b
Source dataset
uspto-grants-1978_04
Patent number
US04082851

Reaction notes

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