Ketene → HCID 13138219, compound

HRID 1262800Notes

Reaction equation

HRID 1262800 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].[CH2:24]=[C:25]=[O:26]>ClCCl>[C:25]([NH: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])(=[O:26])[CH3:24]

Participants

4

Reactant 2

HCID 10038KeteneHCID 131382142-Amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

Product 1

HCID 13138219HCID 13138219, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide (1.0 g) suspended in 25 ml of dichloromethane was treated with ketene for 10 minutes (ca. 0.4 mole/hr). The mixture was allowed to stand and after 15 minutes a light orange solution resulted. Evaporation of the solvent gave an orange glassy oil which was triturated with water and allowed to stand for 16 hours. The white solid thus obtained was removed by filtration and dried in-vacuo to yield 0.24 g of the desired product, m.p. 161°-162°. The product showed absorption peaks by proton NMR at 4.0 (singlet, 3H); 2.5 (singlet, 3H) and 2.1 (singlet, 3H) consistent for the acetylated derivative. The infrared absorption spectrum showed peaks at 1700, 1695, 1610 and 1580 also confirming the desired acylation.

Workup

  1. customa light orange solution resulted
  2. customEvaporation of the solvent
  3. customgave an orange glassy oil which
  4. customwas triturated with water
  5. waitto stand for 16 hours
  6. customThe white solid thus obtained
  7. customwas removed by filtration
  8. customdried in-vacuo

Sources & evidence

ORD record
ord-e1d6b437c37e4daa97f80827320f5feb
Source dataset
uspto-grants-1984_06
Patent number
US04453971

Reaction notes

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