2-Chlorobenzoyl chloride → HCID 19973948, compound

HRID 1451157Notes

Reaction equation

HRID 1451157 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][C:12]([C:21]1[N:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[N:22]=1)([CH:18]([CH3:20])[CH3:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N(C(C)C)C(C)C)C>C(OCC)(=O)C>[CH3:20][CH:18]([CH3:19])[C:12]([C:21]1[N:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[N:22]=1)([NH:11][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[Cl:1])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 691102-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 19973933HCID 19973933, compound

Product 1

HCID 19973948HCID 19973948, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2-Chlorobenzoyl chloride (0.35 g) in ethyl acetate (3 ml) was added to a stirred solution of ethyl 2-amino-3-methyl-2-(4,6-dimethoxypyrimidin-2-yl)butanoate (0.566 g) and ethyl diisopropylamine (0.258 g) in ethyl acetate (15 ml). The mixture was stirred at room temperature for 2 hours, filtered, and the filtrate was washed with water, dried and evaporated to dryness under vacuum. The residual solid was triturated with 60°-80° petroleum ether to give 0.4 g of the desired product as a white solid, mp 94°-95° C.

Workup

  1. filtrationfiltered
  2. washthe filtrate was washed with water
  3. customdried
  4. customevaporated to dryness under vacuum
  5. customThe residual solid was triturated with 60°-80° petroleum ether

Sources & evidence

ORD record
ord-9014cdabd073464189630e4f4bee26bc
Source dataset
uspto-grants-1997_02
Patent number
US05604181

Reaction notes

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