Ammonium Hydroxide → HCID 9903565, compound

HRID 843668Notes

Reaction equation

HRID 843668 reaction equation
C[O:2][C:3]([C:5]1[C:9]([O:10][CH2:11][CH2:12][CH3:13])=[CH:8][S:7][C:6]=1[NH:14][C:15]([N:17]([CH3:19])[CH3:18])=[O:16])=O.[OH-].[NH4+:21]>C(O)C>[CH3:18][N:17]([CH3:19])[C:15](=[O:16])[NH:14][C:6]1[S:7][CH:8]=[C:9]([O:10][CH2:11][CH2:12][CH3:13])[C:5]=1[C:3]([NH2:21])=[O:2]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 53648704HCID 53648704, compound

Product 1

HCID 9903565HCID 9903565, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 2-(3,3-Dimethyl-ureido)-4-propoxy-thiophene-3-carboxylic acid methyl ester ( ) in ethanol (6 mL) was treated with concentrated ammonium hydroxide (6 mL) in a sealed tube and heated to 40° C. for 5 hours. The mixture was then cooled, evaporated, acidified with a small amount of acetic acid and purified via radial chromatography on a 2 mm plate using hexanes/ethyl acetate (3/1) plus 2% methanol as eluent to afford a white solid (15 mg, 55.3 micromol, 51%) 1H NMR (CDCL3, 400 MHz) 1.03 (t, 3H, J=7.3 Hz), 1.81-1.88 (m, 2H), 3.04 (s, 6H), 3.97 (t, 2H, J=6.6 Hz), 5.33 (broad s, 1H), 5.55 (s, 1H), 7.50 (broad s, 1H), 12.00 (s, 1H).

Workup

  1. temperatureThe mixture was then cooled
  2. customevaporated
  3. custompurified via radial chromatography on a 2 mm plate

Sources & evidence

ORD record
ord-542f691bd130482a9cd4d0e8dc421f6c
Source dataset
uspto-grants-2002_04
Patent number
US06380214B1

Reaction notes

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