Sulfuric Acid → HCID 53923417, compound

HRID 1977830Notes

Reaction equation

HRID 1977830 reaction equation
C(OC(=O)[NH:5][C:6]1[S:10][N:9]=[C:8]([S:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:7]=1[C:17]#[N:18])C.S(=O)(=O)(O)[OH:21]>>[NH2:5][C:6]1[S:10][N:9]=[C:8]([S:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:7]=1[C:17]([NH2:18])=[O:21]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 53955720HCID 53955720, compound

Product 1

HCID 53923417HCID 53923417, compoundYield 100%

Conditions

Temperature
100 °C

Procedure

A mixture of (4-Cyano-3-pentylsulfanyl-isothiazol-5-yl)-carbamic acid ethyl ester (2.7 g, 9.0 mmol) and concentrated sulfuric acid (5 mL) was heated to 100° C. for 6 hours. After cooling to ambient temperature, the mixture was diluted with ice water, extracted three times with ethyl acetate, and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo, affording 2.2 g (100%) of 5-amino-3-pentylsulfanyl-isothiazole-4-carboxylic acid amide as a yellow oil. 1H NMR (400 MHz, CDCl3) δ3.26 (t, 2H, J=7.2 Hz), 1.71 (m, 2H), 1.43-1.19 (m, 4H), 0.88 (t, 3H, J=6.8 Hz) ppm.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted three times with ethyl acetate
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4b0a3a05e0f4110a69078198d9ca52a
Source dataset
uspto-grants-2001_05
Patent number
US06235764B1

Reaction notes

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