Riluzole → HCID 14099490, compound

HRID 1904167Notes

Reaction equation

HRID 1904167 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:16][C:17]1[C:18]([O:20][C:21](=O)[C:22]=1[CH3:23])=[O:19].C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[F:14][C:12]([F:15])([F:13])[O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([N:1]3[C:18](=[O:19])[C:17]([CH3:16])=[C:22]([CH3:23])[C:21]3=[O:20])[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 5070RiluzoleHCID 7583Diphenyl EtherHCID 13010Dimethylmaleic anhydride

Product 1

HCID 14099490HCID 14099490, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A 100 ml flask was charged with 2-amino-6-trifluoromethoxybenzothiazole (7.03 g), 2,3-dimethylmaleic anhydride (4.16 g) and diphenyl ether (50 ml), and a Dean-Stark separator was attached to the flask. The reaction materials were refluxed for about 5 minutes. After allowing the reaction mixture to cool, it was poured into hexane (200 ml). The resulting crystals were collected by filtration and washed with a small amount of diethyl ether to give N-(6-trifluoromethoxy-2-benzothiazolyl)-dimethymaleimide (7.66 g). m.p. 196°-198° C.

Workup

  1. temperatureThe reaction materials were refluxed for about 5 minutes
  2. temperatureto cool
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with a small amount of diethyl ether

Sources & evidence

ORD record
ord-c274a6cb88fa44b8a9d1148830fb0160
Source dataset
uspto-grants-1989_06
Patent number
US04836844

Reaction notes

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