Dimethylamine → HCID 13646612, compound

HRID 1381060Notes

Reaction equation

HRID 1381060 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]([NH:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([CH3:23])[N:16]=1)=[O:13])(=[O:10])=[O:9].[N:24]([O-])=O.[Na+].[CH3:28][NH:29][CH3:30]>C(O)(=O)C.C(O)(=O)CC.O.Cl>[CH3:28][N:29]([CH3:30])[N:24]=[N:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]([NH:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([CH3:23])[N:16]=1)=[O:13])(=[O:10])=[O:9]

Participants

8

Reactant 3

HCID 674DimethylamineHCID 131382142-Amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamideHCID 23668193Sodium Nitrite

Product 1

HCID 13646612HCID 13646612, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolvent2×HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 1032Propionic AcidSolvent

Procedure

2-Amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide (3.0 g) in acetic acid (30 mL), propionic acid (20 mL), water (10 mL) and concentrated HCl (2.0 mL) was cooled to 0° C. To this mixture was added sodium nitrite (0.75 g) with stirring. The mixture was held at -10° to 0° C. for 45 minutes. The mixture was then added to an ice and water slurry containing dimethylamine (150 mL, 25% dimethylamine in water). The homogeneous solution was acidified with acetic acid and the heavy white precipitate filtered, washed with water and dried in vacuo, to afford 2.94 g of the title compound as a white solid, m.p. 158°-160° C.

Workup

  1. filtrationthe heavy white precipitate filtered
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-271fc6f38298423ab1bddbbc38efff4d
Source dataset
uspto-grants-1986_04
Patent number
US04585470

Reaction notes

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