Water → HCID 59237150, compound

HRID 2380779Notes

Reaction equation

HRID 2380779 reaction equation
[OH-].[NH4+:2].[CH3:3][N:4]([N:6]=[N:7][C:8]1[CH:12]=[CH:11][S:10][C:9]=1[C:13]([O:15]C)=O)[CH3:5].O>C1COCC1>[CH3:3][N:4]([N:6]=[N:7][C:8]1[CH:12]=[CH:11][S:10][C:9]=1[C:13]([NH2:2])=[O:15])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 16639509HCID 16639509, compound

Product 1

HCID 59237150HCID 59237150, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold (0-5° C.) solution of ammonium hydroxide (20 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (600 mg) in THF (5 mL) for 5 min and stirred at rt for 20 h. The solution was poured into ice cooled water and the precipitated solid was filtered and dried to give crude product, which was chromatographed over silica gel column using chloroform-methanol (98:2) as eluents to give the product as an off-white solid (400 mg, 72%), mp 168-170° C. IR (neat) νmax 3337, 3172, 2923, 1636, 1599, 1348, 1219, 1117, 884, 771 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.28 (2H, br s), 7.35 (1H, d, J=5.6 Hz), 7.31 (1H, d, J=5.6 Hz), 3.58 (3H, br s), 3.20 (3H, br s); LC-MS (positive ion mode): m/z 221 (M+Na)+.

Workup

  1. additionThe solution was poured into ice
  2. filtrationthe precipitated solid was filtered
  3. customdried
  4. customto give crude product, which
  5. customwas chromatographed over silica gel column

Sources & evidence

ORD record
ord-d5e6463f0f1d44d7b084ab1f5c84d1f5
Source dataset
uspto-grants-2012_09
Patent number
US08258119B2

Reaction notes

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