Methanesulfonyl isocyanate → HCID 13768039, compound

HRID 1789354Notes

Reaction equation

HRID 1789354 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH:23]3[NH:27][CH2:26][CH2:25][S:24]3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:28][S:29]([N:32]=[C:33]=[O:34])(=[O:31])=[O:30]>CC(C)=O>[CH3:28][S:29]([NH:32][C:33]([N:27]1[CH2:26][CH2:25][S:24][CH:23]1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH2:9][CH2:10]1)=[O:34])(=[O:31])=[O:30]

Participants

4

Reactant 2

HCID 12668338Methanesulfonyl isocyanateHCID 13768101HCID 13768101, compound

Product 1

HCID 13768039HCID 13768039, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.94 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine are dissolved in anhydrous acetone, and 0.73 g of methanesulfonyl isocyanate is added thereto at room temperature. After the mixture is stirred for 30 minutes, the mixture is concentrated under reduced pressure to remove solvent. The residue is collected by filtration, and washed with water and ether, successively. The crude product thus obtained is recrystallized from a mixture of acetone and ether. 1.56 g of N-methanesulfonyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazollidine-3-carboxamide are obtained.

Workup

  1. customat room temperature
  2. concentrationthe mixture is concentrated under reduced pressure
  3. customto remove solvent
  4. filtrationThe residue is collected by filtration
  5. washwashed with water and ether
  6. customThe crude product thus obtained
  7. customis recrystallized from a mixture of acetone and ether

Sources & evidence

ORD record
ord-4309e47a359d4d8aa7980c2c2a42a140
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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