2-Isocyanato-4-methylthiophene → 1,3-di-n-heptyl-1-N-4-methylthiophenylcarbamyl-2-S-ethyl isothiourea

HRID 2198461Notes

Reaction equation

HRID 2198461 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].[CH3:21][C:22]1[CH:23]=[C:24]([N:27]=[C:28]=[O:29])[S:25][CH:26]=1>C(N(CC)CC)C.C(Cl)Cl>[CH2:14]([N:13]([C:28](=[O:29])[NH:27][C:24]1[S:25][CH:26]=[C:22]([CH3:21])[CH:23]=1)[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 71278012-Isocyanato-4-methylthiopheneHCID 13064686HCID 13064686, compound

Product 1

HCID 1317128591,3-di-n-heptyl-1-N-4-methylthiophenylcarbamyl-2-S-ethyl isothiourea

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

The equipment was the same as in Example 26 above. 3.0 g (0.01 mole) 1,3-di-n-heptyl-2-S-ethyl isothiourea was mixed with 25 ml of methylene chloride. Two drops of triethylamine and 1 drop of dibutyltindilaurate were added and then 1.65 g (0.01 mole) 4-methyl thiophenyl isocyanate was added. The temperature rose from 23° to 33°. The reaction mixture was then vacuum evaporated to remove the methylene chloride to produce 4.65 g (100 percent of theory yield) of a yellow liquid having a nD30 of 1.5340. The liquid solidified on standing into a semi-solid. The product was identified as the title product by IR and NMR spectra analyses. Compound No. in Table 47 in Table I.

Workup

  1. customrose from 23° to 33°
  2. customvacuum evaporated
  3. customto remove the methylene chloride
  4. customto produce
  5. custom4.65 g (100 percent of theory yield) of a yellow liquid

Sources & evidence

ORD record
ord-4403f3607b2a41359e8840b189c1163c
Source dataset
uspto-grants-1982_11
Patent number
US04357351

Reaction notes

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