M-Cresol → Deferiprone

HRID 1578674Notes

Reaction equation

HRID 1578674 reaction equation
C1C([OH:7])=CC=CC=1C.[CH:9]1[C:14]([N:15]=[C:16]=O)=[CH:13][CH:12]=[C:11]([O:18]C2C=CC(N=C=O)=CC=2)[CH:10]=1.ClCl>>[CH3:9][C:10]1[N:15]([CH3:16])[CH:14]=[CH:13][C:12](=[O:7])[C:11]=1[OH:18]

Participants

4

Reactant 3

HCID 342M-CresolHCID 24526ChlorineHCID 613321,1'-Oxybis(4-isocyanatobenzene)

Product 1

HCID 2972Deferiprone

Procedure

Using the method described in Example 8, 240 g of m-cresol are mixed with 50.4 g of 4,4'-diisocyanatodiphenyl ether followed by 70.6 g of 4,4'-bis-α-chloroacetamidodiphenylether at 120°C and the mixture is then reacted at 185°C for 14 hours. 346 g of an approximately 30% polyhydantoin solution which has a chlorine content below 0.2% and a viscosity of 12460 cP20°C are obtained. Precipitation of this solution in methanol yields 210 g of a polyhydantoin with a nitrogen content of 10.4% and a chlorine content below 0.2%. The hydantoin structure is in both cases confirmed by the IR absorption bands at 1700 and 1755 cm-1.

Workup

  1. customthe mixture is then reacted at 185°C for 14 hours

Sources & evidence

ORD record
ord-b2f78f03cb4c485ea802056230b3cf69
Source dataset
uspto-grants-1976_02
Patent number
US03939122

Reaction notes

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