4-Nitrobenzenesulfonyl chloride → HCID 15539132, compound

HRID 382772Notes

Reaction equation

HRID 382772 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): δ 2.29 (s, 1 H), 2.84, 3.47 {AB q of d, J=12.4(3.8) Hz, 12.4(7.9) Hz, 4 H}, 3.30 (m, 1 H), 4.46, 5.07 (AB q, J=12.5 Hz, 2 H), 5.31 (s, 1 H), 8.11, 8.41 (AB q, J=8.7 Hz, 8 H); 13C NMR (DMSO-d6): δ 50.0, 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-cf69d65206dd47ac8fa37ff1c0b87061
Source dataset
uspto-grants-2001_10
Patent number
US06310204B1

Reaction notes

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