Phenyl chloroformate → HCID 67297557, compound

HRID 628998Notes

Reaction equation

HRID 628998 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[N:7][CH:8]=1.C(=O)(O)[O-].[Na+].Cl[C:28]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29]>C(OCC)(=O)C>[C:31]1([O:30][C:28](=[O:29])[NH:15][C:12]2[CH:13]=[CH:14][C:9]([C:6]3[N:5]=[C:4]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[C:3]([O:2][CH3:1])=[CH:8][N:7]=3)=[CH:10][CH:11]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 67295475HCID 67295475, compound

Product 1

HCID 67297557HCID 67297557, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(5-methoxy-4-morpholin-4-yl-pyrimidin-2-yl)-phenylamine (1.50 g, 1.0 eq.) and sodium bicarbonate solution (6 ml) in ethyl acetate (6 ml) stirring 5 min. After dropping phenyl chloroformate (0.98 ml, 1.2 eq) for 4 hrs at room temperature. The resultant mixture extracted with EA and the combined organic layers were washed with brine and dried in vacuo to give a light brown solid (1.80 g, 40.5%) as the product.

Workup

  1. customfor 4 hrs
  2. customat room temperature
  3. extractionThe resultant mixture extracted with EA
  4. washthe combined organic layers were washed with brine
  5. customdried in vacuo

Sources & evidence

ORD record
ord-057e951a1ccc4f2caa4ffe8affb00efa
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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