Hydrochloric Acid → N-[2,6-Bis(1-methylethyl)-4-phenoxyphenyl]thiourea

HRID 358831Notes

Reaction equation

HRID 358831 reaction equation
Cl.[O:2]([C:9]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[C:12]([NH2:13])=[C:11]([CH:19]([CH3:21])[CH3:20])[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[S-:22][C:23]#[N:24].[Na+].O.Cl>CC1C=CC=CC=1C>[O:2]([C:9]1[CH:10]=[C:11]([CH:19]([CH3:21])[CH3:20])[C:12]([NH:13][C:23]([NH2:24])=[S:22])=[C:14]([CH:16]([CH3:17])[CH3:18])[CH:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 516871Sodium thiocyanateHCID 200672734-Phenoxy-2,6-diisopropylaniline hydrochloride

Product 1

HCID 15753006N-[2,6-Bis(1-methylethyl)-4-phenoxyphenyl]thioureaYield 96%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

305 g (1 mol) of 4-phenoxy-2,6-diisopropylaniline hydrochloride, 97 g (1.2 mol) of sodium thiocyanate, 10 ml of water and 10 ml of concentrated hydrochloric acid are suspended in 800 ml of o-xylene. The mixture is heated to 90° C. over 6 hours, during which time 2 ml of concentrated hydrochloric acid are added after 3 hours and then after each further hour. Thereafter the reaction mixture is cooled to room temperature and the product is isolated by filtration, washed with water and dried, giving 315 g (96% of theory) of N-(4-phenoxy-2,6-diisopropylphenyl)thiourea in the form of pale grey crystals which melt at 219°-221° C.

Workup

  1. additionare added after 3 hours
  2. waitafter each further hour
  3. customthe product is isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-a47fdd02837c4936a52439a966a570fd
Source dataset
uspto-grants-1991_03
Patent number
US04997967

Reaction notes

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