Water → HCID 22070930, compound

HRID 2259635Notes

Reaction equation

HRID 2259635 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[NH:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=1[O:24][CH3:25].C(N(CC)CC)C.[C:33](Cl)(Cl)=[S:34].O>C(Cl)Cl>[CH3:25][O:24][C:15]1[CH:16]=[CH:17][C:18]([C:20]([F:21])([F:22])[F:23])=[CH:19][C:14]=1[N:13]1[C:4]2[CH:5]=[CH:6][C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:3]=2[NH:2][C:33]1=[S:34]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 131719220HCID 131719220, compound

Product 1

HCID 22070930HCID 22070930, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled suspension of N-(2-amino-4-trifluoromethylphenyl)-2-methoxy-5-trifluoromethylaniline, hydrochloride (3 mmol, 1.2 g) in dry methylenechloride (20 ml) is added triethylamine (9 mmol, 0.73 ml) and thiophosgene (3 mmol, 0.23 ml). The reaction mixture is stirred at room temperature overnight and poured into water. The mixture is extracted with methylenechloride and the organic phases are dried and concentrated in vacuo. The crude product is subjected to column chromatography using petroleum ether+ethylacetate (4+1) as eluent. The fractions containing the product are concentrated in vacuo yielding a yellow oil which solidifies upon treatment with petroleum ether, yielding the title compound as off white crystals, which were used without further purification.

Workup

  1. extractionThe mixture is extracted with methylenechloride
  2. customthe organic phases are dried
  3. concentrationconcentrated in vacuo
  4. additionThe fractions containing the product
  5. concentrationare concentrated in vacuo
  6. customyielding a yellow oil which

Sources & evidence

ORD record
ord-414d2929cd9f47708fa5d1ab83d57593
Source dataset
uspto-grants-1995_12
Patent number
US05475015

Reaction notes

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