Citric Acid → Benzyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(4-chlorophenyl)-4-pyrimidinyl]-amide

HRID 10258Notes

Reaction equation

HRID 10258 reaction equation
CC(C)([O-])C.[K+].Cl[C:8]1[N:13]=[CH:12][N:11]=[C:10]([NH:14][S:15](=[O:25])(=[O:24])[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]=1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1.C(O)(=O)C[C:35](CC(O)=O)([C:37](O)=[O:38])[OH:36]>C(O)CO>[OH:36][CH2:35][CH2:37][O:38][C:8]1[N:13]=[CH:12][N:11]=[C:10]([NH:14][S:15](=[O:25])(=[O:24])[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]=1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 21979544Benzyl sulfamic acid-[6-chloro-5-(p-chloro-phenyl)-4-pyrimidinyl]-amideHCID 23665647Potassium tert-butoxide

Product 1

HCID 21979542Benzyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(4-chlorophenyl)-4-pyrimidinyl]-amide

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
102 °C

Procedure

Potassium tert.-butoxide (3.5 g) was dissolved in ethyleneglycol (35 ml), benzyl sulfamic acid-[6-chloro-5-(4-chlorophenyl)-4-pyrimidinyl]-amide (1.8 g, Referential Example 15) was added and the mixture was heated to 102° C. for 11 h. The mixture was poured onto ice/water and acidified to pH=4 with solid citric acid. The precipitated product was filtered off, washed with water and dried at HV to give benzyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(4-chlorophenyl)-4-pyrimidinyl]-amide (1.77 g). tR=4.36 (LC); [M+H]+=435.09 (ES+).

Workup

  1. additionThe mixture was poured onto ice/water
  2. filtrationThe precipitated product was filtered off
  3. washwashed with water
  4. customdried at HV

Sources & evidence

ORD record
ord-acd75006bb814bdab99020ebd9053b27
Source dataset
uspto-grants-2006_08
Patent number
US07094781B2

Reaction notes

Loading…