Triethylamine → 1,3-Di(2,2,2-trifluoroethyl)thiourea

HRID 34804

Reaction equation

HRID 34804 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][N:4]=[C:5]=[S:6].Cl.[F:10][C:11]([F:15])([F:14])[CH2:12][NH2:13].C(N(CC)CC)C>C(#N)C>[F:1][C:2]([F:8])([F:7])[CH2:3][NH:4][C:5]([NH:13][CH2:12][C:11]([F:15])([F:14])[F:10])=[S:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethane

Product 1

HCID 117764131,3-Di(2,2,2-trifluoroethyl)thiourea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,2,2-Trifluoroethylisothiocyanate (2.12 g.) was added to a mixture of 2,2,2-trifluoroethylamine hydrochloride (1.36 g), triethylamine (1.01 g) and acetonitrile (10 ml.), and the mixture stirred at room temperature for 4 hours and then evaporated to dryness. The residue was partitioned between water and ethyl acetate, and the ethyl acetate phase was dried and evaporated to dryness. The residue was recrystallised from a mixture of acetone and light petroleum ether (b.p. 60°-80°) to give 1,3-di(2,2,2-trifluoroethyl)thiourea, m.p. 152°-153°.

Workup

  1. customevaporated to dryness
  2. customThe residue was partitioned between water and ethyl acetate
  3. dry with materialthe ethyl acetate phase was dried
  4. customevaporated to dryness
  5. customThe residue was recrystallised from a mixture of acetone and light petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-291331072b234f3eae842ce3a0c3e233
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Linked notes

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