Sulfuric Acid → HCID 53861315, compound

HRID 750553Notes

Reaction equation

HRID 750553 reaction equation
[C:1]([C:3]1[C:4]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[N:5][S:6][C:7]=1[NH:8][C:9](=[O:13])[N:10]([CH3:12])[CH3:11])#[N:2].S(=O)(=O)(O)[OH:22]>>[CH3:11][N:10]([CH3:12])[C:9](=[O:13])[NH:8][C:7]1[S:6][N:5]=[C:4]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:3]=1[C:1]([NH2:2])=[O:22]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 18550181HCID 18550181, compound

Product 1

HCID 53861315HCID 53861315, compoundYield 78%

Procedure

A mixture of 3-(4-cyano-3-hexylsulfanyl-isothiazol-5-yl)-1,1-dimethyl-urea (0.09 g, 0.29 mmol) and concentrated sulfuric acid (0.18 mL) was stirred at ambient temperature for 1.5 hours. The mixture was diluted with ice water, extracted three times into ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo affording 0.076 g (78%) of 5-(3,3-dimethyl-ureido)-3-hexylsulfanyl-isothiazole-4-carboxylic acid amide as a colorless solid: 1H NMR (300 MHz, acetone-d6) δ 7.08 (bs, 2H), 3.20 (t, 2H, J=7.2 Hz), 3.02 (s, 6H), 1.63 (p, 2H, J=7.2 Hz), 1.35 (m, 2H), 1.23 (m, 4H) 0.78 (t, 3H, J=6.9 Hz) ppm; MS (APCl, m/z): 331 [M+H]+.

Workup

  1. extractionextracted three times into ethyl acetate
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ba4e21816024bd2bbf8f85d51dde6f9
Source dataset
uspto-grants-2008_07
Patent number
US07405218B2

Reaction notes

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