tert-Butyl isocyanate → 1,3-di-n-heptyl-1-N-tert-butylcarbamyl-2-S-ethyl isothiourea

HRID 462477Notes

Reaction equation

HRID 462477 reaction equation
[CH2:1]([NH:8][C:9](=[N:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[S:10][CH2:11][CH3:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:21]([N:25]=[C:26]=[O:27])([CH3:24])([CH3:23])[CH3:22]>C(N(CC)CC)C.C(Cl)Cl>[CH2:14]([N:13]([C:26](=[O:27])[NH:25][C:21]([CH3:24])([CH3:23])[CH3:22])[C:9](=[N:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[S:10][CH2:11][CH3:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 13064686HCID 13064686, compound

Product 1

HCID 130835081,3-di-n-heptyl-1-N-tert-butylcarbamyl-2-S-ethyl isothiourea

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

The equipment was the same as used in Example 26. 3.0 g (0.01 mole) 1,3-di-n-heptyl-2-S-ethyl isothiourea was mixed with 30 ml of methylene chloride. Two drops of triethylamine and 1 drop of dibutyltindilaurate were added to the mixture followed by 1.0 g (0.01 mole) tert-butyl isocyanate. The temperature rose from 24° to 39° C. The reaction mixture was stirred overnight at ambient temperature and then heated for one-half hour at 35° to 40° C. to complete the reaction. The reaction mixture was vacuum evaporated to produce 3.83 g (96 weight percent of theory yield) of a clear liquid having a nD30 of 1.4750. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 40 in Table I.

Workup

  1. customrose from 24° to 39° C
  2. temperatureheated for one-half hour at 35° to 40° C.
  3. customthe reaction
  4. customevaporated
  5. customto produce
  6. custom3.83 g (96 weight percent of theory yield) of a clear liquid

Sources & evidence

ORD record
ord-08f1e8cece9a457dbf7e230dfd0f0595
Source dataset
uspto-grants-1985_05
Patent number
US04515813

Reaction notes

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