Ethyl isocyanate → 2,6-Dichloro-4-[2-(3-ethyl-ureido)-4-methyl-thiazol-5-yl]-benzenesulfonamide

HRID 2247326Notes

Reaction equation

HRID 2247326 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[NH2:6][C:7]1[S:8][C:9]([C:13]2[CH:18]=[C:17]([Cl:19])[C:16]([S:20]([NH2:23])(=[O:22])=[O:21])=[C:15]([Cl:24])[CH:14]=2)=[C:10]([CH3:12])[N:11]=1>CN(C)C=O>[Cl:24][C:15]1[CH:14]=[C:13]([C:9]2[S:8][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[N:11][C:10]=2[CH3:12])[CH:18]=[C:17]([Cl:19])[C:16]=1[S:20]([NH2:23])(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanate2×HCID 858616664-(2-Amino-4-methyl-thiazol-5-yl)-2,6-dichloro-benzenesulfonamide

Product 1

HCID 865984032,6-Dichloro-4-[2-(3-ethyl-ureido)-4-methyl-thiazol-5-yl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl isocyanate (0.015 ml, 0.19 mmol) is added to a stirred solution of 4-(2-amino-4-methyl-thiazol-5-yl)-2,6-dichloro-benzenesulfonamide (Example 26) (0.043 g, 0.127 mmol) in dry dimethylformamide (1.0 ml) under argon. After heating at 85° C. for 3 hours more ethyl isocyanate (0.015 ml, 0.19 mmol) is added and heating continued for a further hour. The reaction is concentrated in vacuo and the product is purified by chromatography on silica eluting with ethyl acetate—hexane (1:1 increasing to 4:1) to give the title compound. MH+ (TOF, MS, ES+): 408.9, 410.9, 412.8

Workup

  1. additionis added
  2. temperatureheating
  3. waitcontinued for a further hour
  4. concentrationThe reaction is concentrated in vacuo
  5. customthe product is purified by chromatography on silica eluting with ethyl acetate—hexane (1:1 increasing to 4:1)

Sources & evidence

ORD record
ord-e168de1c4a654e5bafed6ee82906e350
Source dataset
uspto-grants-2010_03
Patent number
US07687637B2

Reaction notes

Loading…