Formic Acid → HCID 15029618, compound
Reaction equation
[CH:1](OC(=O)C)=[O:2].C(O)=O.C(OC(=O)C)(=O)C.[CH3:17][O:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]=1[CH:29]([S:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:30][NH2:31]>C1COCC1>[C:33]1([S:32][CH:29]([C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:27]=[CH:28][C:19]=2[O:18][CH3:17])[CH2:30][NH:31][CH:1]=[O:2])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Acetic formic anhydride is generated by dropwise addition of 98% formic acid (1472 mg, 32 mmol) to 2655 mg (26 mmol) of acetic anhydride maintained at 0° C. followed by gentle heating at 50°-60° C. for 2 h. The mixture is cooled to -15° C. and 20 ml of THF are added. To the resulting solution is added dropwise at -15° C. a solution of 1-(2-methoxynaphth-1-yl)-1-(phenylthio)-2-aminoethane (3094 mg, 10 mmol) in THF (50 ml). The reaction mixture is allowed to warm to room temperature and the volatiles are removed in vacuo. The residue is taken up in ether. The ether solution is washed with water and NaHCO3 solution, dried over anhydrous K2CO3 and then evaporated in vacuo. The oily residue is triturated with ethyl acetate-hexane mixture to give crystalline title compound in 85% yield (2870 mg).
Workup
- temperatureby gentle heating at 50°-60° C. for 2 h
- temperatureThe mixture is cooled to -15° C.
- temperatureto warm to room temperature
- customthe volatiles are removed in vacuo
- washThe ether solution is washed with water and NaHCO3 solution
- dry with materialdried over anhydrous K2CO3
- customevaporated in vacuo
- customThe oily residue is triturated with ethyl acetate-hexane mixture
Sources & evidence
- ORD record
- ord-a6931ddf07844ed4a4083d34701d95e5
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05122537
Reaction notes
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