Sodium Iodide → HCID 86606143, compound

HRID 2102816Notes

Reaction equation

HRID 2102816 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[S:9]1[C:13]2[CH:14]=[C:15]([NH2:18])[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[NH2:19].[I-].[Na+].C(N(C(C)C)C(C)C)C.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][C:34]=1[N:40]=[C:41]=[O:42]>CN(C=O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:18][C:15]2[CH:16]=[CH:17][C:12]3[N:11]=[C:10]([NH:19][C:41]([NH:40][C:34]4[CH:35]=[C:36]([CH3:39])[CH:37]=[CH:38][C:33]=4[O:32][CH3:31])=[O:42])[S:9][C:13]=3[CH:14]=2)[CH:7]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 215042,6-BenzothiazolediamineHCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 41415202-Isocyanato-1-methoxy-4-methylbenzene

Product 1

HCID 86606143HCID 86606143, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4,6-dichloropyrimidine (180 mg, 1.21 mmol), benzothiazole-2,6-diamine (200 mg, 1.21 mmol), sodium iodide (216 mg, 1.45 mmol), ethyl diisopropylamine (0.25 mL, 1.45 mmol) and DMF (10 mL) was heated at 85° C. for 3 h. 2-Methoxy-5-methylphenyl isocyanate (0.20 mL, 1.33 mmol) was added and heating was continued at 85° C. for 3 h. The solvent was removed and the residue treated with CH2Cl2. The precipitate was separated (0.57 g, 85%). LC/ESI-MS: m/z=441 [M+H]+; m/z=439 [M−H]−; Rt=3.64 min.

Workup

  1. temperatureheating
  2. customThe solvent was removed
  3. additionthe residue treated with CH2Cl2
  4. customThe precipitate was separated (0.57 g, 85%)

Sources & evidence

ORD record
ord-35f2958e765b4eca8a5fa6a3190a51c4
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Reaction notes

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