Sulfuric Acid → HCID 21900912, compound

HRID 2044148Notes

Reaction equation

HRID 2044148 reaction equation
N[C:2](N)=[S:3].[N+]([O-])([O-])=O.[NH4+].O1[CH2:27][CH:11]1[CH2:12][S:13][CH2:14][CH:15]1[CH2:20][S:19][CH:18]([CH2:21][S:22][CH2:23][CH:24]2OC2)[CH2:17][S:16]1.[S:28](=O)(=O)(O)O>C1(C)C=CC=CC=1.CO>[S:3]1[CH2:2][CH:24]1[CH2:23][S:22][CH2:21][CH:18]1[CH2:17][S:16][CH:15]([CH2:14][S:13][CH2:12][CH:11]2[S:28][CH2:27]2)[CH2:20][S:19]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 22985Ammonium nitrateHCID 2723790ThioureaHCID 219006152,5-Bis[[(2-oxiranylmethyl)thio]methyl]-1,4-dithiane

Product 1

HCID 21900912HCID 21900912, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

305 g of thiourea, 3000 ml of methanol, 1500 ml of toluene, 10 g of ammonium nitrate, and 373 g of 2,5-bis(β-epoxypropylthiomethyl)-1,4-dithiane were mixed and reacted at 20° C. for 9 hours in a nitrogen atmosphere. During the reaction, no polymer was deposited. After the reaction, 3800 ml of toluene and 460 ml of 10% aqueous solution of sulfuric acid were put to the reaction vessel to extract the reaction product. Then, the extracted product was washed with 300 ml of water four times, and toluene was removed by distillation. As a result, 340 g of 2,5-bis(β-epithiopropylthiomethyl)-1,4-dithiane (in formula (6), p=1, q=1) was obtained. The yield was 83%. The results are shown in Table 4.

Workup

  1. customreacted at 20° C. for 9 hours in a nitrogen atmosphere
  2. customDuring the reaction
  3. extractionto extract the reaction product
  4. washThen, the extracted product was washed with 300 ml of water four times, and toluene
  5. customwas removed by distillation

Sources & evidence

ORD record
ord-612a949417ed41d3a5cf2ee16a23b09e
Source dataset
uspto-grants-2013_11
Patent number
US08586766B2

Reaction notes

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