Hydrochloric Acid → Iprodione

HRID 617015

Reaction equation

HRID 617015 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17](=[O:23])[NH:18][CH2:19][C:20]([OH:22])=O)[CH:12]=[C:13]([Cl:15])[CH:14]=1.Cl.[CH:25]([N:28]=[C:29]=[O:30])([CH3:27])[CH3:26]>ClC1C=CC=CC=1>[CH:25]([NH:28][C:29]([N:18]1[CH2:19][C:20](=[O:22])[N:16]([C:11]2[CH:12]=[C:13]([Cl:15])[CH:14]=[C:9]([Cl:8])[CH:10]=2)[C:17]1=[O:23])=[O:30])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 595293N-[[(3,5-dichlorophenyl)amino]carbonyl]glycine

Product 1

HCID 37517IprodioneYield 100.6%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
50 °C

Procedure

101 g of triethylamine are added to a suspension of 263 g of 2-[3-(3,5-dichlorophenyl)-ureido]-acetic acid in 2,000 cm3 of chlorobenzene and 300 g of isopropyl isocyanate, which has been heated to 50° C, and the mixture is stirred for 4 hours at 80°-90°. After cooling, the reaction mixture is stirred for 30 minutes with 500 cm3 of a 7% strength (weight/volume) aqueous solution of hydrochloric acid. The organic solution is decanted, dried and concentrated under reduced pressure. 332 g of 1-isopropylcarbamoyl-3-(3,5-dichlorophenyl)-hydantoin melting at 130° C are thus obtained.

Workup

  1. temperatureAfter cooling
  2. customThe organic solution is decanted
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9783e2e49edf49a3a030f93600e2b706
Source dataset
uspto-grants-1978_02
Patent number
US04076941

Linked notes

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