3,4-Dichlorophenyl isocyanate → HCID 59149951, compound

HRID 655553Notes

Reaction equation

HRID 655553 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.Cl.[N:14]1([CH2:20][CH2:21][CH2:22][N:23]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25][S:24]2(=[O:31])=[O:30])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:27]2[CH2:26][CH2:25][S:24](=[O:30])(=[O:31])[N:23]([CH2:22][CH2:21][CH2:20][N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[CH2:29][CH2:28]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 76073,4-Dichlorophenyl isocyanateHCID 8471TriethylamineHCID 67080688HCID 67080688, compound2×

Product 1

HCID 59149951HCID 59149951, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3,4-dichlorophenyl isocyanate (59 mg, 0.31 mmol) in tetrahydrofuran (0.5 ml) was added dropwise at room temperature to a suspension of 2-(3-piperidin-1-yl-propyl)-[1,2,5]thiadiazepane 1,1-dioxide dihydrochloride (intermediate 13; 100 mg, 0.29 mmol) and triethylamine (116 mg, 1.15 mmol) in tetrahydrofuran (2 ml). The reaction mixture was stirred for 16 h, then partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; dichloro-methane/methanol/25% aq. ammonia solution 95:5:0.25) produced the title compound (117 mg, 88%). White solid, MS (ISP)=463.0 (M+H)+.

Workup

  1. custompartitioned between sat. aq. ammonium chloride solution and ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-3430f3d42fe64bc2b8979ac17a527f41
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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