Phenol → HCID 86736852, compound

HRID 1701078Notes

Reaction equation

HRID 1701078 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]1([OH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:15][C:16]1[N:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[N:17]=1>C1(C)C(C)=CC=CC=1.C(Cl)Cl>[C:8]1([O:14][S:2](=[O:4])(=[O:3])[NH:5][C:6]([NH:15][C:16]2[N:17]=[C:18]([O:24][CH3:25])[CH:19]=[C:20]([O:22][CH3:23])[N:21]=2)=[O:7])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 70918Chlorosulfonyl isocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidine

Product 1

HCID 86736852HCID 86736852, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 7237O-XyleneSolvent

Procedure

To a well stirred solution of 1.6 g of chlorosulfonyl isocyanate in 7 ml of dry xylene at ambient temperature and pressure was added 0.9 g of phenol. The resulting mixture was heated to reflux temperature for 1.5 hours. The solvent was removed under reduced pressure to give a clear oil. The oil was diluted with 5 ml of methylene chloride and added to a cooled (ice-water bath) suspension of 1.5 g of 2-amino-4.6-dimethoxypyrimidine in 10 ml of methylene chloride. The solvent was removed under vacuum. The resultant oil was triturated with 1-chlorobutane and filtered to yield 2.6 g of white solid, m.p. 136°-139° C. The infrared spectrum showed characteristic absorption bands at 3150 cm-1, 1720 cm-1, 1625 cm-1, 1580 cm-1.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux temperature for 1.5 hours
  3. customThe solvent was removed under reduced pressure
  4. customto give a clear oil
  5. additionadded to
  6. temperaturea cooled
  7. customThe solvent was removed under vacuum
  8. customThe resultant oil was triturated with 1-chlorobutane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-855a9dad1ec6493dbde0fc300dd79eb6
Source dataset
uspto-grants-1980_03
Patent number
US04191553

Reaction notes

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