2-Thiazolamine, 4-(trifluoromethyl)- → Benzamide, 2,6-dichloro-N-(((4-(trifluoromethyl)-2-thiazolyl)amino)carbonyl)-

HRID 261183Notes

Reaction equation

HRID 261183 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1[N:4]=[C:5]([NH2:8])[S:6][CH:7]=1.[Cl:11][C:12]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:13]=1[C:14]([N:16]=[C:17]=[O:18])=[O:15]>C(OC(=O)C)C>[Cl:11][C:12]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:13]=1[C:14]([NH:16][C:17]([NH:8][C:5]1[S:6][CH:7]=[C:3]([C:2]([F:10])([F:9])[F:1])[N:4]=1)=[O:18])=[O:15]

Participants

4

Reactant 2

HCID 12014172-Thiazolamine, 4-(trifluoromethyl)-HCID 129127392,6-Dichlorobenzoyl isocyanate

Product 1

HCID 13422728Benzamide, 2,6-dichloro-N-(((4-(trifluoromethyl)-2-thiazolyl)amino)carbonyl)-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 1.7 g (0.01 mole) of 4-trifluoromethyl-2-aminothiazole in 50 ml of dry ethylacetate was added all at once to a solution of 2.16 g (0.01 mole) of freshly prepared 2,6-dichlorobenzoylisocyanate dissolved in 10 ml of dry ethylacetate. The mixture was allowed to stir at 25° for 4 hours. The solvent was evaporated in vacuo, ether was added to the residue, and the solid was removed by filtration to give 3.7 g of product, m.p. 210°-213°. The infrared and nuclear magnetic resonance spectra were consistent with the proposed structure.

Workup

  1. customThe solvent was evaporated in vacuo, ether
  2. additionwas added to the residue
  3. customthe solid was removed by filtration

Sources & evidence

ORD record
ord-be49ba30bdb1483ab7da7314c174ac7e
Source dataset
uspto-grants-1979_08
Patent number
US04164581

Reaction notes

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