6-Isocyanato-2,2,4,4-tetrefluoro-1,3-benzodioxene → HCID 59252134, compound

HRID 658496Notes

Reaction equation

HRID 658496 reaction equation
[CH:1]1[C:6]([N:7]=[C:8]=[O:9])=[CH:5][C:4]2[C:10]([F:17])([F:16])[O:11][C:12]([F:15])([F:14])[O:13][C:3]=2[CH:2]=1.[CH3:18][O:19][C:20]([C:22]1[CH:27]=[C:26]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([NH2:35])[CH:30]=2)[CH:25]=[CH:24][N:23]=1)=[O:21]>C(Cl)Cl>[F:14][C:12]1([F:15])[O:13][C:3]2[CH:2]=[CH:1][C:6]([NH:7][C:8]([NH:35][C:31]3[CH:30]=[C:29]([CH:34]=[CH:33][CH:32]=3)[O:28][C:26]3[CH:25]=[CH:24][N:23]=[C:22]([C:20]([O:19][CH3:18])=[O:21])[CH:27]=3)=[O:9])=[CH:5][C:4]=2[C:10]([F:16])([F:17])[O:11]1

Participants

4

Reactant 2

HCID 27752076-Isocyanato-2,2,4,4-tetrefluoro-1,3-benzodioxeneHCID 60125954HCID 60125954, compound

Product 1

HCID 59252134HCID 59252134, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2,2,4,4-tetrafluoro-6-isocyanato-1,3-benzodioxene (0.816 g, 3.28 mmol) was added 4-(3-aminophenoxy)pyridine-2-carboxylic acid methyl ester (0.800 g, 3.28 mmol) in DCM (13 mL) in portions. The homogenous contents turned white and opaque within 1 min. of addition, and were allowed to stir at room temperature for 12 h. The heterogenous mixture was filtered, and solid product repeatedly washed with DCM to remove residual starting material. The desired product was collected as a white powder, 1.36 g (83%). 1H-NMR (DMSO-d6) δ 9.08 (d, 2H), 8.59 (s, 1H), 8.07 (s, 1H), 7.60 (dd, 1H), 7.37 (m, 4H), 7.25 (d, 1H), 7.20 (dd, 1H), 6.80 (d, 1H), 3.82 (s, 3H); MS LC MS [M+H]+=494.1, RT=3.23 min.

Workup

  1. additionThe homogenous contents turned white and opaque within 1 min. of addition
  2. filtrationThe heterogenous mixture was filtered
  3. washsolid product repeatedly washed with DCM
  4. customto remove residual
  5. customThe desired product was collected as a white powder, 1.36 g (83%)

Sources & evidence

ORD record
ord-e9a50958289a44729aba07b748ec6cc4
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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