2,6-Difluorophenyl isothiocyanate → HCID 20513898, compound

HRID 1902862Notes

Reaction equation

HRID 1902862 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]=[C:10]=[S:11].[CH2:12]([O:19][NH:20][CH2:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1C=CC=CC=1>[CH2:12]([O:19][N:20]([CH2:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33])[C:10]([NH:9][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])=[S:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 40316012,6-Difluorophenyl isothiocyanateHCID 18787878N-{2-[(benzyloxy)amino]ethyl}phthalimide

Product 1

HCID 20513898HCID 20513898, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 19.68 g of 2,6-difluorophenylisothiocyanate and 34.1 g of N-{2-[N-(benzyloxy)amino]ethyl}phthalimide in 150 ml of benzene is heated to boiling under reflux for 6 hours. The cooled solution is separated from a slight precipitate and then evaporated in vacuo. The residual oil crystallizes from isopropyl ether. There is obtained 1-(benzyloxy)-3-(2,6-difluorophenyl)-1-(2-phthalimidoethyl)-2-thiourea of melting point 141°-143° (ether/methylene chloride).

Workup

  1. temperatureunder reflux for 6 hours
  2. customThe cooled solution is separated from a slight precipitate
  3. customevaporated in vacuo
  4. customThe residual oil crystallizes from isopropyl ether

Sources & evidence

ORD record
ord-6a68f3bbdd1e4d8f97c16e54e8fc6437
Source dataset
uspto-grants-1982_12
Patent number
US04366160

Reaction notes

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