Ammonium formate → HCID 15290001, compound

HRID 1735893Notes

Reaction equation

HRID 1735893 reaction equation
O[CH2:2][C:3]1[N:7]([C@H:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([F:19])=[CH:13][C:14]=3[F:18])[CH2:9]2)[C:6](=[S:20])[NH:5][CH:4]=1.[CH:21]([O-:23])=O.[NH4+:24]>O>[F:18][C:14]1[CH:13]=[C:12]([F:19])[CH:11]=[C:10]2[C:15]=1[CH2:16][CH2:17][C@H:8]([N:7]1[C:3]([CH2:2][NH:24][CH:21]=[O:23])=[CH:4][NH:5][C:6]1=[S:20])[CH2:9]2

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 15290000HCID 15290000, compound

Product 1

HCID 15290001HCID 15290001, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of (S)-5-hydroxymethyl-1-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (1.0 g, 3.5 mmol), prepared as in Example 18, and ammonium formate (10 g, 158.6 mmol) was stirred at approximately 125° C. for 1 hour. The mixture was then heated to approximately 138° C. and stirred for an additional 35 minutes. The mixture was diluted with 25 mL of water and allowed to cool to room temperature. The mixture was aged for approximately 18 hours giving a crystalline material. The material was isolated by filtration and the filter residue was washed with water. Drying to constant weight gave (S)-N-[3-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazol-4-ylmethyl]formamide (0.92 g, 2.96 mmol).

Workup

  1. temperatureThe mixture was then heated to approximately 138° C.
  2. stirringstirred for an additional 35 minutes
  3. temperatureto cool to room temperature
  4. waitThe mixture was aged for approximately 18 hours
  5. customgiving a crystalline material
  6. customThe material was isolated by filtration
  7. washthe filter residue was washed with water
  8. customDrying to constant weight

Sources & evidence

ORD record
ord-2ed26d2cb9ec481894f12260cdc8b8ce
Source dataset
uspto-grants-1996_07
Patent number
US05538988

Reaction notes

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