Water → HCID 178489911, compound

HRID 2248444Notes

Reaction equation

HRID 2248444 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([NH2:11])=[C:5]([NH2:12])[C:4]=1[CH3:13].C(N(CC)CC)C.[C:21](Cl)(Cl)=[S:22].O>C(Cl)(Cl)Cl>[CH3:13][C:4]1[C:5]2[N:12]=[C:21]([SH:22])[NH:11][C:6]=2[C:7]([CH3:10])=[C:8]([CH3:9])[C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 10040ThiophosgeneHCID 19996505HCID 19996505, compound

Product 1

HCID 178489911HCID 178489911, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 4-methoxy-3,5,6-trimethyl-1,2-phenylenediamine (1.8 g, 0.010 mol) and triethylamine (2.1 g, 0.021 mol) in CHCl3 (15 ml) was added dropwise to a stirred solution of thiophosgene (0.60 g, 0.0052 mol) in CHCl3 (5 ml). The mixture was then stirred at room temperature for 1 hour. Water (15 ml) and triethylamine (0.5 g) was added and the mixture was stirred for 1 hour. The precipitate was filtered off, washed with water and dried in the air giving the desired product (0.96 g, 43%), NMR: δ (CDCl3) 2.5 (s,3H), 2.65(s,6H), 3.65(s,3H), 12.0(br.s.,1H).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried in the air

Sources & evidence

ORD record
ord-f22a9b64b05149ec813a91be8a940b2d
Source dataset
uspto-grants-1991_08
Patent number
US05039806

Reaction notes

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