Triethylamine → HCID 18930607, compound

HRID 1598902Notes

Reaction equation

HRID 1598902 reaction equation
Br.[NH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])=[O:5].[C:21]([C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26])#[N:22].Cl[C:31](Cl)([O:33]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>O1CCCC1>[C:21]([C:23]1[CH:24]=[C:25]([NH:26][C:31](=[O:33])[NH:2][CH2:3][C:4]([NH:6][C:7]2[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=2[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[O:5])[CH:27]=[CH:28][CH:29]=1)#[N:22]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 167023-AminobenzonitrileHCID 94429TriphosgeneHCID 376124HCID 376124, compound

Product 1

HCID 18930607HCID 18930607, compoundYield 204.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the compound 3a (1.341 g, 4 mmol) prepared in Preparation 3 in tetrahydrofuran (10 ml) is added under ice cooling to a solution of m-bromoisocyanate which is prepared according to the method described in EP-508796-A1 from a solution of m-cyanoaniline (581 mg, 4.92 mmol), triphosgene (551 mg, 1.72 mmol) and triethylamine (960 μl, 6.9 mmol) in tetrahydrofuran (50 ml). In addition, triethylamine (558 μl, 4 mmol) is added and treated as in a manner similar to that described in Preparation 5 to prepare the compound 6w (1.4 g, yield 88%).

Workup

  1. customis prepared
  2. additiontreated as in a manner similar to
  3. customthat described in Preparation 5

Sources & evidence

ORD record
ord-cac8aa0c9bba456f8350e6dfc12a4c57
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

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