Formic Acid → HCID 131723672, compound

HRID 2297329Notes

Reaction equation

HRID 2297329 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14](\[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[CH2:15][CH2:16][Cl:17])=[CH:9][CH:8]=1)[CH3:3].[CH:30]([OH:32])=[O:31]>C(OCC)C>[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10](/[C:13](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14](\[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)/[CH2:15][CH2:16][Cl:17])=[CH:11][CH:12]=1)[CH3:3].[CH:30]([O-:32])=[O:31]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 3005573Toremifene

Product 1

HCID 131723672HCID 131723672, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of toremifene base (1.00 g, 0.0025 moles) and refluxing diethyl ether (14 ml) was slowly added formic acid (100 μl, 0.0027 moles). The refluxing mixture was stirred for a while and cooled to room temperature. The mixture was stirred additional 30 min at room temperature. The salt was crystallised at −15° C. for 36 hours. After filtration the formate of toremifene was obtained (yield 78%) having melting point of 147° C. 1H-NMR (d6-DMSO) d 8.19 (s, 1H), 7.39 (t, 2H), 7.35-7.27 (m, 3H), 7.27-7.12 (m, 5H), 6.76 (d, 2H), 6.62 (d, 2H), 3.95 (t, 2H), 3.43 (t, 2H 2.85 (t, 2H), 2.70 (t, 2H), 2.28 (s, 6H).

Workup

  1. stirringThe mixture was stirred additional 30 min at room temperature
  2. customThe salt was crystallised at −15° C. for 36 hours
  3. filtrationAfter filtration the formate of toremifene
  4. customwas obtained (yield 78%)

Sources & evidence

ORD record
ord-ff34940571594f7996bf334a5c850c4c
Source dataset
uspto-grants-2002_12
Patent number
US06491951B1

Reaction notes

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