Triethylamine → N-[4-(Methylsulfanyl)phenyl]-N'-propan-2-ylsulfuric diamide

HRID 1760523Notes

Reaction equation

HRID 1760523 reaction equation
[CH3:1][CH:2]([NH:4][S:5](Cl)(=[O:7])=[O:6])[CH3:3].[CH3:9][S:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[CH3:9][S:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][S:5]([NH:4][CH:2]([CH3:3])[CH3:1])(=[O:7])=[O:6])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660384-(Methylthio)anilineHCID 117737Isopropylsulphamoyl chloride

Product 1

HCID 54434743N-[4-(Methylsulfanyl)phenyl]-N'-propan-2-ylsulfuric diamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-Methylethyl)sulfamoyl chloride (6.63 g, 0.034 mol) was added dropwise to a solution of 4-(methylthio) aniline (4.48 g, 0.032 mol) and triethylamine (4.87 ml, 0.035 mol) in dry dichloromethane (100 ml) at 0° C. under a nitrogen atmosphere. After addition, the resultant mixture was allowed to warm to room temperature and was stirred for 6 hr. The reaction mixture was further extracted with dichloromethane and the organic extracts washed with water (2×50 ml), dried (MgSO4) and concentrated in vacuo to yield N-(4-methylthiophenyl)-N′-(1-methylethyl)sulfamide as a white solid. δ (1H NMR, DMSO, ppm): 0.8 (6H, d), 2.3 (3H, s), 3.2 (1H, m), 3.35 (1H, s), 6.9-7.1 (4H, m), 9.5 (1H, s). M.P. 65-68° C.

Workup

  1. additionAfter addition
  2. extractionThe reaction mixture was further extracted with dichloromethane
  3. washthe organic extracts washed with water (2×50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4062e787cf0425199abcecf3244ce5a
Source dataset
uspto-grants-2005_01
Patent number
US06844338B2

Reaction notes

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