4-Chlorophenyl Isocyanate → HCID 25002089, compound

HRID 659001Notes

Reaction equation

HRID 659001 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:29]=[CH:28][C:15]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])[N:18]=2)=[CH:14][CH:13]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])[N:18]=3)=[CH:28][CH:29]=2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 67524085HCID 67524085, compound

Product 1

HCID 25002089HCID 25002089, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 159 mg (1.033 mmol) 4-chlorophenyl isocyanate in 3 ml THF was given at 0° C. to a solution of 269 mg (1.033 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in 5 ml THF within 10 min. After stirring overnight the reaction mixture was evaporated and the residue purified by chromatography on silica gel (ethyl acetate). The obtained material was recrystallized from 9 ml methanol to give 69 mg (16%) of the title compound.

Workup

  1. customwas evaporated
  2. customthe residue purified by chromatography on silica gel (ethyl acetate)
  3. customThe obtained material was recrystallized from 9 ml methanol

Sources & evidence

ORD record
ord-15bf381cee7c4068b4497ab212db2d6b
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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