Ammonium Hydroxide → HCID 10490982, compound

HRID 2226852Notes

Reaction equation

HRID 2226852 reaction equation
[CH3:1][CH:2]([S:4][C:5]1[C:6]2[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=2[S:8][C:9]=1[C:10](O)=[O:11])[CH3:3].C1N=C[N:19](C(N2C=NC=C2)=O)C=1.[NH4+].[OH-]>C1COCC1>[CH3:1][CH:2]([S:4][C:5]1[C:6]2[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=2[S:8][C:9]=1[C:10]([NH2:19])=[O:11])[CH3:3]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 139616693-[(1-Methylethyl)thio]benzo[b]thiophene-2-carboxylic acid

Product 1

HCID 10490982HCID 10490982, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-[(1-methylethyl)thio]benzo[b]thiophene-2-carboxylic acid (133 mg, 0.53 mmol) [Connor D. T., et al., U.S. Pat. No. 4,703,053 (1987)] in 6 mL of THF is added N,N-carbonyldiimidazole (99 mg, 0.61 mmol). The mixture is heated at reflux for 1.5 hours then cooled slightly. Aqueous NH4OH (1 mL) is added and the reaction mixture is stirred at room temperature for 30 minutes, then partitioned between ethyl acetate and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography eluting with 1:1 hexane:ethyl acetate to provide 3-[(1-methylethyl)thio]benzo[b]thiophene-2-carboxamide in 83% yield; mp=183-185° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 1.5 hours
  3. temperaturethen cooled slightly
  4. custompartitioned between ethyl acetate and brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by flash chromatography
  9. washeluting with 1:1 hexane

Sources & evidence

ORD record
ord-cdae854420d048bea78cb25c63a3e8af
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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