Benzoyl isocyanate → HCID 66745791, compound

HRID 471620Notes

Reaction equation

HRID 471620 reaction equation
[NH2:1][C:2]1[S:10][C:5]2[CH2:6][O:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]#[N:12].[C:13]([N:21]=[C:22]=[O:23])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCOCC1>[C:11]([C:3]1[C:4]2[CH2:9][CH2:8][O:7][CH2:6][C:5]=2[S:10][C:2]=1[NH:1][C:22]([NH:21][C:13](=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:23])#[N:12]

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 7377432-Amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carbonitrile

Product 1

HCID 66745791HCID 66745791, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carbonitrile (Example 146b) (400 mg, 2.22 mmol) in 1,4-dioxane (30 mL) was added benzoyl isocyanate (327 mg, 2.22 mmol). The reaction mixture was then stirred at room temperature under nitrogen overnight. The precipitate was collected by filtration, washed with 1,4-dioxane, and dried in the air to give the title compound (577 mg, 80%) as a light yellow solid. NMR (400 MHz, DMSO-d6) δ 2.62 (t, J=5.2 Hz, 2H), 3.87 (t, J=5.2 Hz, 2H), 4.62 (s, 2H), 7.56-7.53 (m, 2H), 7.67-7.65 (m, 1H), 8.04-8.01 (m, 2H), 11.60 (brs, 1H), 12.13 (brs, 1H).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with 1,4-dioxane
  3. customdried in the air

Sources & evidence

ORD record
ord-7146f66c4c7e42288611fd00bdc2b490
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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