Diisopropylethylamine → Benzyl sulfamic acid-[6-chloro-5-(p-chloro-phenyl)-4-pyrimidinyl]-amide

HRID 10247Notes

Reaction equation

HRID 10247 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[K].[CH2:26]([NH:33][S:34](=[O:37])(=[O:36])[NH2:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CS(C)=O.CO>[Cl:15][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:35][S:34](=[O:36])(=[O:37])[NH:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 219795694,6-Dichloro-5-(4-chlorophenyl)-pyrimidineHCID 68727905Benzylsulfamic acid amide potassium salt

Product 1

HCID 21979544Benzyl sulfamic acid-[6-chloro-5-(p-chloro-phenyl)-4-pyrimidinyl]-amideYield 44.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

To 4,6-dichloro-5-(4-chloro-phenyl)-pyrimidine (Referential Example 9) (2.59 g) dissolved in DMSO (14 ml) was added di-isopropyl-ethyl-amine (1.8 ml) followed by the addition of benzyl sulfamic acid amide potassium salt (2.25 g) [prepared from the product described in Referential Example 22 and potassium tert.-butylate in methanol followed by the evaporation of the solvent]. The mixture was stirred for 24 h at rt then poured onto water (300 ml) and diethylether (120 ml) was added and the solution was stirred for 30 min. The layers were separated and the water layer was acidified with solid citric acid (pH=3) and cooled to 0° C. for 1 h. The precipitated product was filtered off, washed with water and recrystallized from methanol to give benzyl sulfamic acid-[6-chloro-5-(p-chloro-phenyl)-4-pyrimidinyl]-amide (1.8 g). tR=4.94 min (LC); [M+H]+410.90 (ES+);

Workup

  1. customprepared from the product
  2. customfollowed by the evaporation of the solvent]
  3. additionthen poured onto water (300 ml) and diethylether (120 ml)
  4. additionwas added
  5. stirringthe solution was stirred for 30 min
  6. customThe layers were separated
  7. temperaturecooled to 0° C. for 1 h
  8. filtrationThe precipitated product was filtered off
  9. washwashed with water
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-101c7ac50baf4d4999c44b012e398b23
Source dataset
uspto-grants-2006_08
Patent number
US07094781B2

Reaction notes

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