Water → 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (dibutylaminothio)methylcarbamate

HRID 1065212Notes

Reaction equation

HRID 1065212 reaction equation
[CH2:1]([N:5]([CH2:8][CH2:9][CH2:10][CH3:11])[S:6]Cl)[CH2:2][CH2:3][CH3:4].[CH3:12][NH:13][C:14](=[O:27])[O:15][C:16]1[C:24]2[O:23][C:22]([CH3:26])([CH3:25])[CH2:21][C:20]=2[CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.O>CCCCCC.C(N(CC)CC)C.S(=O)=O>[CH2:1]([N:5]([CH2:8][CH2:9][CH2:10][CH3:11])[S:6][CH2:12][NH:13][C:14](=[O:27])[O:15][C:16]1[C:24]2[O:23][C:22]([CH3:25])([CH3:26])[CH2:21][C:20]=2[CH:19]=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 2566CarbofuranHCID 8471Triethylamine2×HCID 81031Amidosulfenyl chloride, N,N-dibutyl-

Product 1

HCID 132063912,3-Dihydro-2,2-dimethyl-7-benzofuranyl (dibutylaminothio)methylcarbamateYield 90%

Reagents, catalysts & solvents 2

HCID 12824984Triethylamine sulfur dioxideCatalystHCID 8058HexaneSolvent

Conditions

Temperature
11 °C

Procedure

A flask was charged with 30.2 g of a 50% solution of dibutylaminosulfenyl chloride (0.077 mole) in hexane and 15.8 g of 98% 2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate (0.07 mole) was added. Triethylamine (7.8 g, 0.077 mole) was added to the mixture with agitation over a period of seven minutes. A temperature rise from 24.5° to 26° C. was observed. A portion (1.9 g, 0.0115 mole) of the triethylamine/sulfur dioxide catalyst prepared in Example 3 was added dropwise. The temperature gradually rose to 30° C., and was raised further by external heating to 35° C. for a total reaction time of 100 minutes from the beginning of triethylamine addition. Twenty minutes later the mixture was cooled to 11° C. and 31 ml of water was added and mixed. The mixture was filtered to remove a small amount of solid, separated, and the organic layer was concentrated to yield 26.64 g of 90% (hplc) 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (dibutylaminothio)methylcarbamate (a 90% chemical yield based on the starting carbamate).

Workup

  1. additionwas added
  2. customfrom 24.5° to 26° C.
  3. customgradually rose to 30° C.
  4. temperaturewas raised further
  5. additionmixed
  6. filtrationThe mixture was filtered
  7. customto remove a small amount of solid
  8. customseparated
  9. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-07ad1bb7582f4de9bbc9893b077fb3b8
Source dataset
uspto-grants-1982_05
Patent number
US04329293

Reaction notes

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