Benzenesulfonyl chloride → HCID 68552384, compound

HRID 1432350Notes

Reaction equation

HRID 1432350 reaction equation
C1(S(Cl)(=O)=O)C=CC=CC=1.O[C:12]1([C:22]2(C(O)=O)[CH2:30][C:26]3[N:27]=[CH:28][S:29][C:25]=3[CH2:24][CH2:23]2)[CH2:21][CH2:20][CH2:19][C:18]2[N:17]=[CH:16][N:15]=[CH:14][C:13]1=2>N1C=CC=CC=1>[S:29]1[C:25]2[CH2:24][CH2:23][C:22](=[C:12]3[CH2:21][CH2:20][CH2:19][C:18]4[N:17]=[CH:16][N:15]=[CH:14][C:13]3=4)[CH2:30][C:26]=2[N:27]=[CH:28]1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 68548420HCID 68548420, compound

Product 1

HCID 68552384HCID 68552384, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
140 °C

Procedure

1.06 g of benzenesulphonyl chloride is added to a solution of 0.66 g of 5-(5-hydroxy-5,6,7,8-tetrahydroquinazoline-5-yl)-4,5,6,7-tetrahydrobenzothiazole-5-carboxylic acid and 20 ml of pyridine at 0° C. After 2 hours at 0° C., the reaction mixture is poured into ice-water—the resulting solid is filtered off, dried, dissolved in 1 ml of 2,4,6-trimethylpyridine and then heated to 140° C. After 90 minutes, the reaction mixture is cooled to room temperature, mixed with hot water, stirred for 10 minutes and then the water is decanted off. This “water-treatment process” is repeated twice more. The solid is then dried and purified by flash chromatography (SiO2 60F). The title compound is identified on the basis of e Rf.

Workup

  1. filtrationis filtered off
  2. customdried
  3. dissolutiondissolved in 1 ml of 2,4,6-trimethylpyridine
  4. waitAfter 90 minutes
  5. temperaturethe reaction mixture is cooled to room temperature
  6. additionmixed with hot water
  7. customthe water is decanted off
  8. customThe solid is then dried
  9. custompurified by flash chromatography (SiO2 60F)

Sources & evidence

ORD record
ord-47c5dc6a28174034bb536847edb9c247
Source dataset
uspto-grants-2009_11
Patent number
US07612088B2

Reaction notes

Loading…