2-Aminothiophenol → HCID 54486421, compound

HRID 973442Notes

Reaction equation

HRID 973442 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[CH2:9]=[C:10]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)[C:11]([OH:13])=[O:12]>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][CH:10]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][CH:15]=1)[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 18963482HCID 18963482, compound

Product 1

HCID 54486421HCID 54486421, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20.41 g of aminothiophenol were added all at once to a solution of 43 g of α-methylene-4-(trifluoromethyl)-benzene acetic acid [J. Med. Chem. (1969), Vol. 12 (3), p. 477 to 480] in 300 ml of ethanol, and the mixture was refluxed for 2 hours. The ethanol was evaporated off and the residue was taken up in 600 ml of ethyl ether and partially concentrated to 300 ml. 200 ml of isopropyl ether were added with concentration to 100 ml and cooled for 30 minutes in ice-cooled water. The crystallized product was separated off, washed with isopropyl ether and dried under reduced pressure at 100° C. to obtain 21.9 g of expected product melting at approx. 138° C.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customThe ethanol was evaporated off
  3. concentrationpartially concentrated to 300 ml
  4. addition200 ml of isopropyl ether were added with concentration to 100 ml
  5. temperaturecooled for 30 minutes in ice-
  6. temperaturecooled water
  7. customThe crystallized product was separated off
  8. washwashed with isopropyl ether
  9. customdried under reduced pressure at 100° C.

Sources & evidence

ORD record
ord-601f0df2f35e426595aeafe6ad821740
Source dataset
uspto-grants-1991_11
Patent number
US05063225

Reaction notes

Loading…