4-Nitrobenzenesulfonyl chloride → HCID 15539132, compound

HRID 1937737Notes

Reaction equation

HRID 1937737 reaction equation
[NH:1]1[CH2:6][CH:5]([OH:7])[CH2:4][NH:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)([O-:16])=[O:15]>O.C1(C)C=CC=CC=1>[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:1]2[CH2:6][CH:5]([OH:7])[CH2:4][N:3]([S:23]([C:20]3[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:22][CH:21]=3)(=[O:24])=[O:25])[CH2:2]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 10953438HCID 10953438, compound

Product 1

HCID 15539132HCID 15539132, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Procedure

A solution of hexahydro-5-pyrimidinol (1.0 g, 9.8 mmol) and sodium carbonate (1.04 g, 9.8 mmol) in 10 mL of water in a 250 mL round bottom flask was stirred with a magnetic stir bar for 10 minutes. A solution of 4-nitrobenzenesulfonyl chloride (4.4 g, 19.8 mmol) in 10 mL of toluene was added dropwise over a period of 30 minutes. The reaction mixture formed a white suspended solid. A mixture of 100 mL of water and 20 mL of toluene was added to the reaction mixture and stirred overnight. The reaction mixture was filtered and the solid was washed with 100 mL of toluene, then with 100 mL of water. The solid was dried at room temperature under reduced pressure to give 4.4 g (95%) of crude product, hexahydro-1,3-bis(4-nitrobenzenesulfonyl)-5-pyrimidinol. [1H NMR (DMSO-d6): δ2.29 (s, 1H), 2.84, 3.47 {AB q of d, J=12.4(3.8) Hz, 12.4(7.9) Hz, 4H}, 3.30 (m, 1H), 4.46, 5.07 (AB q, J=12.5 Hz, 2H), 5.31 (s, 1H), 8.11, 8.41 (AB q, J=8.7 Hz, 8H); 13C NMR (DMSO-d6): δ50.0, 59.8, 60.6, 124.6, 128.9, 143.3, 150.1].

Workup

  1. customThe reaction mixture formed
  2. additionwas added to the reaction mixture
  3. filtrationThe reaction mixture was filtered
  4. washthe solid was washed with 100 mL of toluene
  5. customThe solid was dried at room temperature under reduced pressure

Sources & evidence

ORD record
ord-5cfe5c34ae3c4abfbb12c94acb1e79de
Source dataset
uspto-grants-2002_05
Patent number
US06395899B2

Reaction notes

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