Ammonium formate → HCID 67107513, compound

HRID 2177724Notes

Reaction equation

HRID 2177724 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][CH3:22])[C:14]([C:23](=O)[CH2:24]Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:27]([O-:29])=O.[NH4+:30]>C(O)=O.O>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][CH3:22])[C:14]([C:23]3[N:30]=[CH:27][O:29][CH:24]=3)=[CH:13][CH:12]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86677112HCID 86677112, compound2×

Product 1

HCID 67107513HCID 67107513, compoundYield 27.8%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 6-(benzenesulphonylmethyl)-3-(2-bromoacetyl)-2-methoxy-benzoate (Intermediate 51, 0.9 g) and ammonium formate (0.45 g) in formic acid (5 ml) was sealed in a vial and heated at 80° C. for 3 hours then at 100° C. for 6 hours. After standing at room temperature overnight, the mixture was heated at 120° C. for 4 hours. The mixture was diluted with water and extracted with ethyl acetate, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl 6-(benzenesulphonylmethyl)-3-(oxazol-4-yl)-2-methoxy-benzoate (0.22 g) as a yellow gum which was used directly without further purification or characterisation.

Workup

  1. customwas sealed in a vial and
  2. waitAfter standing at room temperature overnight
  3. temperaturethe mixture was heated at 120° C. for 4 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-115b976239ba4e1a8fb606f6d0c1ef2d
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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