Water → 3-Chloro-N,N-bis[(4-methoxyphenyl)methyl]-1-propanesulfonamide

HRID 1972289Notes

Reaction equation

HRID 1972289 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[CH3:9][O:10][C:11]1[CH:27]=[CH:26][C:14]([CH2:15][NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1.CCN(CC)CC.O>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([N:16]([CH2:15][C:14]1[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:27][CH:26]=1)[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 714952Bis(4-methoxybenzyl)amine

Product 1

HCID 594857113-Chloro-N,N-bis[(4-methoxyphenyl)methyl]-1-propanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloropropane-1-sulfonyl chloride (1.46 g, 8.22 mmol) in anhydrous CH2Cl2 (20 mL) at 0° C. is added bis-(4-methoxy-benzyl)-amine (2.22 g, 8.63 mmol) followed by Et3N (1.68 g, 10.69 mmol). After the addition, the mixture is allowed to warm to room temperature and is stirred for 2 h. The mixture is then poured into water (50 mL) and is extracted with CH2Cl2 (3×50 mL). The combined organic layers are concentrated and purified by flash column chromatography (silica gel, EtOAc/hexane 0%˜50%) to provide 3-chloro-N,N-bis(4-methoxybenzyl)propane-1-sulfonamide as colorless oil. (2.7 g, 84%).

Workup

  1. additionAfter the addition
  2. extractionis extracted with CH2Cl2 (3×50 mL)
  3. concentrationThe combined organic layers are concentrated
  4. custompurified by flash column chromatography (silica gel, EtOAc/hexane 0%˜50%)

Sources & evidence

ORD record
ord-1ae41332160d48d381abc030fbf2a4f2
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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