Phenyl isocyanate → HCID 13787392, compound

HRID 2413928Notes

Reaction equation

HRID 2413928 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[N:14][C:15]([Cl:21])=[CH:16][CH:17]=2)[N:12]=1>O1CCCC1>[Cl:21][C:15]1[N:14]=[C:13]2[C:18]([CH:19]=[CH:20][C:11]([NH:10][C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:9])=[N:12]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13787392HCID 13787392, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Phenyl isocyanate (15.5 g) is added to a solution of 2-amino-7-chloro-1,8-naphthyridine (17.9 g) in anhydrous tetrahydrofuran (600 cc) and the mixture is heated for 15 hours at approximately 60° C. After cooling the mixture, the crystallized solid is separated by filtration, washed with ethyl ether (3×50 cc) and air-dried. A crude product (25.2 g), m.p. 270° C., is obtained. This product (15 g) is purified under the following conditions: the product is dissolved in a mixture of dimethylformamide (200 cc) and acetonitrile (125 cc). After cooling for 5 hours at 20° C., the crystallized solid is separated by filtration, washed with acetonitrile (3×50 cc) and dried at 40° C. under reduced pressure (0.07 kPa). N-(7-Chloro-1,8-naphthyridin-2-yl)-N'-phenylurea (10.1 g), m.p. 276° C., is obtained.

Workup

  1. temperatureAfter cooling the mixture
  2. customthe crystallized solid is separated by filtration
  3. washwashed with ethyl ether (3×50 cc)
  4. customair-dried
  5. customA crude product (25.2 g), m.p. 270° C., is obtained
  6. customThis product (15 g) is purified under the following conditions
  7. dissolutionthe product is dissolved in a mixture of dimethylformamide (200 cc) and acetonitrile (125 cc)
  8. temperatureAfter cooling for 5 hours at 20° C.
  9. customthe crystallized solid is separated by filtration
  10. washwashed with acetonitrile (3×50 cc)
  11. customdried at 40° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-786b92ce5d944ac6b12fbd3ae0dcee9b
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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