Water → Cloturin

HRID 2413889Notes

Reaction equation

HRID 2413889 reaction equation
O.[SH:2][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[NH:5][CH:6]=[N:7]2.C(N(CC)CC)C.[Cl:19][CH2:20][CH2:21][N:22]=[C:23]=[O:24].O>CN(C)C=O>[Cl:19][CH2:20][CH2:21][NH:22][C:23]([S:2][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[NH:5][CH:6]=[N:7]2)=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 178527204HCID 178527204, compound

Product 1

HCID 128676CloturinYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
15 °C

Procedure

A suspension of 6-mercaptopurine monohydrate (17.0 g, 0.1 mole) in dimethylformamide (150 ml) is treated with triethylamine (10.1 g, 0.1 mole) and the solid is dissolved by warming of the mixture to 50°-60° C. The solution is cooled to 15° C. and 2-chloroethylisocyanate (11.6 g, 0.11 mole) is dripped in under cooling with tap water to 15°-20° C. The reaction mixture is stirred at this temperature for 2 hours, and the precipitated product is collected on filter, washed with acetone and dried under reduced pressure at a temperature of approx. 50° C. to give 20.7 g (80%) of the title compound Ia, melting at 221°-223° C. UV absorption spectrum (in dimethylsulfoxide), λ max 326 nm (log ε4.33).

Workup

  1. dissolutionthe solid is dissolved
  2. temperatureby warming of the mixture to 50°-60° C
  3. temperatureunder cooling
  4. customto 15°-20° C
  5. customthe precipitated product is collected
  6. filtrationon filter
  7. washwashed with acetone
  8. customdried under reduced pressure at a temperature of approx. 50° C.

Sources & evidence

ORD record
ord-8afdc2acaff846b390943c6b584390f8
Source dataset
uspto-grants-1988_01
Patent number
US04720497

Reaction notes

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