Hydrochloric Acid → 3-Isopropylphenyl (chlorosulfinyl)(methyl)carbamate

HRID 443747Notes

Reaction equation

HRID 443747 reaction equation
[CH3:1][NH:2][C:3](=[O:14])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[CH:6]=1.[S:15](Cl)([Cl:17])=[O:16].Cl>>[Cl:17][S:15]([N:2]([CH3:1])[C:3](=[O:14])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:12])[CH3:13])[CH:6]=1)=[O:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6143M-Cumenyl MethylcarbamateHCID 24386Thionyl Chloride

Product 1

HCID 127288083-Isopropylphenyl (chlorosulfinyl)(methyl)carbamate

Procedure

Four grams 3-isopropylphenyl methylcarbamate were mixed with excess thionyl chloride and heated up to 80° C. until HCl evolution ceased. Excess thionyl chloride was removed by distillation and the residue was subjected to high vacuum (0.1 mm) for 1 hour. NMR of the residue in chloroform-d-TMS gave the following absorptions: δ7.5-6.9 (m, 4H, aromatic protons). δ3.25 (s, 3H, NCH3), δ3.2-2.7 (m, 1H, CH), and δ1.3-1.2 (d, 6H, C(CH3)2).

Workup

  1. customExcess thionyl chloride was removed by distillation
  2. customNMR of the residue in chloroform-d-TMS gave the following absorptions

Sources & evidence

ORD record
ord-7f1309bf143c4f45a44b3b8e0d836cc6
Source dataset
uspto-grants-1981_04
Patent number
US04261897

Reaction notes

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