Ammonia → 5-Methylthio-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxamide

HRID 2298592Notes

Reaction equation

HRID 2298592 reaction equation
[NH3:1].[CH3:2][S:3][C:4]1[S:8][C:7]([C:9](OC)=[O:10])=[CH:6][C:5]=1[C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1>>[CH3:2][S:3][C:4]1[S:8][C:7]([C:9]([NH2:1])=[O:10])=[CH:6][C:5]=1[C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1

Participants

3

Reactant 2

HCID 222Ammonia2×HCID 18536968Methyl 5-methylthio-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylate

Product 1

HCID 185368675-Methylthio-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxamideYield 88%

Conditions

Temperature
80 °C

Procedure

Liquid ammonia (5 mL) was condensed into a cold (−78° C.) Teflon-lined steel bomb. Methyl 5-methylthio-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylate (0.6 g, 1.7 mmol) as prepared in Example 10 step (a) was introduced in one portion and the bomb was sealed and heated in an oil bath at 80° C. for 48 h. The bomb was cooled to −78° C., opened and the ammonia was allowed to evaporate at room temperature. The residual solid was collected and dried under vacuum to give 0.5 g (88%) of 5-methylthio-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxamide. 1H-NMR (DMSO-d6; 300 MHz) δ2.75 (s, 3H), 7.35-7.40 (m, 1H), 7.40-7.51 (m, 2H), 8.04-8.18 (m, 2H), 8.19 (s, 1H), 8.20 (s, 1H).

Workup

  1. additionwas introduced in one portion
  2. customthe bomb was sealed
  3. temperatureThe bomb was cooled to −78° C.
  4. customto evaporate at room temperature
  5. customThe residual solid was collected
  6. customdried under vacuum

Sources & evidence

ORD record
ord-f9b7cb87a28c493da1e3c7cc07c68674
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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