2,6-Difluorobenzoyl isocyanate → HCID 13246039, compound

HRID 2295791Notes

Reaction equation

HRID 2295791 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[C:19]([Cl:20])=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=2[Cl:21])=[CH:4][CH:3]=1.[F:22][C:23]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:24]=1[C:25]([N:27]=[C:28]=[O:29])=[O:26]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[C:14]([Cl:21])=[CH:15][C:16]([NH:17][C:28]([NH:27][C:25](=[O:26])[C:24]3[C:30]([F:34])=[CH:31][CH:32]=[CH:33][C:23]=3[F:22])=[O:29])=[CH:18][C:19]=2[Cl:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 138271123,5-Dichloro-4-[(4-chloronaphthalen-1-yl)oxy]aniline

Product 1

HCID 13246039HCID 13246039, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution containing 2.25 g (6.6 m moles) of 4-(4-chloro-1-naphthoxy)-3,5-dichloroaniline in 45 ml of toluene was placed under a nitrogen atmosphere and heated to 70° C. via an addition funnel was then added 1.82 g (9.9 m moles) of 2,6-difluorobenzoylisocyanate in 5 ml of toluene. The resulting mixture was then stirred at 70° C. for 45 min. and then cooled to room temperature. It was then cooled below 0° C. and filtered. The collected white white solid was dried under vacuum to afford 1.86 g of the desired product, m.p. 237°-239° C. NMR: (DMSO-d6): δ6.47 (d, J=8 Hz, 1H)- 7.0-8.6 (m, 10H), 10.40 (broad s, 1H), 11.60 (broad s, 1H).

Workup

  1. temperaturecooled to room temperature
  2. temperatureIt was then cooled below 0° C.
  3. filtrationfiltered
  4. customThe collected white white solid was dried under vacuum

Sources & evidence

ORD record
ord-d75c2d1fc4744c92919e62023069afc6
Source dataset
uspto-grants-1984_01
Patent number
US04426385

Reaction notes

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