2-Chloro-N-(2,6-dimethylphenyl)acetamide → HCID 20512450, compound

HRID 1164466Notes

Reaction equation

HRID 1164466 reaction equation
CC1C=CC=C(C)C=1NC#N.[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1[NH:20][C:21]([NH2:23])=S.CC(C)([O-])C.[K+].[Cl:30][CH2:31][C:32]([NH:34][C:35]1[C:40]([CH3:41])=[CH:39][CH:38]=[CH:37][C:36]=1[CH3:42])=[O:33]>CN(C)C=O.O>[ClH:30].[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1[N:20]1[CH2:31][C:32](=[O:33])[N:34]([C:35]2[C:40]([CH3:41])=[CH:39][CH:38]=[CH:37][C:36]=2[CH3:42])[C:21]1=[NH:23]

Participants

7

Reactant 4

HCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamideHCID 8539111-(2,6-Xylyl)thioureaHCID 12652073HCID 12652073, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20512450HCID 20512450, compoundYield 12.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6.3 g (0.0443 moles) of 2,6-dimethylphenyl-cyanamide [m.p.: 120°-122° C.; prepared from 1-(2',6'-dimethylphenyl)-thiourea according to the method of Rathke (Ber. 12, 773 /1879/; Beilstein's Handbuch der organischen Chemie 12 H, 368 /1929/)] are dissolved in 100 ml of dry dimethylformamide, 4.8 g (0.0048 moles) of potassium tert.-butoxide are added, and the mixture is stirred at room temperature for 0.5 hours. Thereafter 8.7 g (0.0443 moles) of N-chloroacetyl-2,6-dimethyl-aniline (m.p.: 145°-146° C.; prepared by acylating 2,6-dimethylaniline with chloroacetyl chloride) are introduced, and the resulting mixture is stirred at 100° C. for 2 hours. The mixture is cooled, poured into water, the separated crystalline product is filtered off, washed with water and dried. This crude product is dissolved in 10% isopropanolic hydrochloric acid, and the salt is precipitated with diethyl ether. 1.7 g (12.5%) of pure 1,3-bis(2',6'-dimethylphenyl)-2-imino-4-oxo-imidazolidine hydrochloride are obtained; m.p.: 219°-221° C.

Workup

  1. stirringthe resulting mixture is stirred at 100° C. for 2 hours
  2. temperatureThe mixture is cooled
  3. filtrationthe separated crystalline product is filtered off
  4. washwashed with water
  5. customdried
  6. dissolutionThis crude product is dissolved in 10% isopropanolic hydrochloric acid
  7. customthe salt is precipitated with diethyl ether

Sources & evidence

ORD record
ord-d2cf60b645d54a07bea8c58ec01dd3d4
Source dataset
uspto-grants-1983_01
Patent number
US04369325

Reaction notes

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