Hydrochloric Acid → 7-Chlorothieno[3,2-b]pyridine-2-carbothioamide

HRID 889891Notes

Reaction equation

HRID 889891 reaction equation
COC[NH:4][C:5]([C:7]1[S:15][C:14]2[C:9](=[N:10][CH:11]=[CH:12][C:13]=2[Cl:16])[CH:8]=1)=[S:6].Cl.[NH4+].[OH-]>C1COCC1>[Cl:16][C:13]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:8]=[C:7]([C:5](=[S:6])[NH2:4])[S:15][C:14]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 858021057-Chloro-thieno[3,2-b]pyridine-2-carbothioic acid methoxymethyl amide

Product 1

HCID 235951097-Chlorothieno[3,2-b]pyridine-2-carbothioamideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-Chloro-thieno[3,2-b]pyridine-2-carbothioic acid methoxymethyl-amide (93.9 g, 344 mmol) and 900 mL THF was added 1 N HCl (344 mL, 344 mmol). The reaction mixture was heated to reflux for seventy-two hours. The reaction mixture was cooled to 0° C., and 300 mL of concentrated NH4OH was added and stirred. The THF was removed under reduced pressure and the residue was suspended in ethyl acetate and stirred. The precipitate was filtered, washed with ethyl acetate and dried to give 7-chloro-thieno[3,2-b]pyridine-2-carbothioic acid amide (66.7 g) in 85% yield. C8H5ClN2S2: APCI m/z: 228.9/230.9 (MH+); 1H NMR (d6-DMSO): δ 10.24 (s, 1H), 9.94 (s, 1H), 8.65 (d, 1H, J=5.0 Hz), 8.19 (s, 1H), 7.62 (d, 1H, J=5.0 Hz) ppm.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for seventy-two hours
  3. customThe THF was removed under reduced pressure
  4. stirringstirred
  5. filtrationThe precipitate was filtered
  6. washwashed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-09de6772c24f47988860595e7be7a232
Source dataset
uspto-grants-2006_02
Patent number
US06995171B2

Reaction notes

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