Acetonitrile → 2-Chloro-N-[(5-chloro-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-3-pyridinesulfonamide

HRID 66449Notes

Reaction equation

HRID 66449 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:10])[C:5]([Cl:9])(C)[CH2:6][N:7]=1.[Cl:11][C:12]1[C:17]([S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1.[C:24](#N)C>>[Cl:11][C:12]1[C:17]([S:18]([NH:21][C:22]([NH:1][C:2]2[N:7]=[C:6]([CH3:24])[C:5]([Cl:9])=[C:4]([CH3:10])[N:3]=2)=[O:23])(=[O:19])=[O:20])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 130384352-Chloro-3-pyridinesulfonylisocyanateHCID 705047302-Amino-5-chloro-5,6-dimethylpyrimidine

Product 1

HCID 204748422-Chloro-N-[(5-chloro-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-3-pyridinesulfonamide

Procedure

To a stirred suspension of 1.4 g of 2-amino-5-chloro-5,6-dimethylpyrimidine in 20 ml of dry acetonitrile at room temperature is added 2.2 g of 2-chloropyridine-3-sulfonylisocyanate. The mixture is stirred for several hours, evaporated to dryness and the residue is mixed with 30 ml of water and enough 10% sodium hydroxide to adjust the pH to 11. This mixture is filtered and the filtrate adjusted to pH 7 by the addition of 10% hydrochloric acid and then refiltered. Acidification of this filtrate to pH 2 causes the desired compound to precipitate. The desired compound is filtered off and dried.

Workup

  1. customevaporated to dryness
  2. additionthe residue is mixed with 30 ml of water and enough 10% sodium hydroxide
  3. filtrationThis mixture is filtered
  4. additionthe filtrate adjusted to pH 7 by the addition of 10% hydrochloric acid
  5. customto precipitate
  6. filtrationThe desired compound is filtered off
  7. customdried

Sources & evidence

ORD record
ord-ae7381d00f9e449496d9db8802d2fc34
Source dataset
uspto-grants-1982_08
Patent number
US04342587

Reaction notes

Loading…