Thiophosgene → HCID 11724583, compound

HRID 1029545Notes

Reaction equation

HRID 1029545 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH3:5][C:6]([C:9]1[CH:10]=[C:11]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[O:12][CH2:13][C:14]([NH:16][NH2:17])=[O:15])([CH3:8])[CH3:7]>O1CCCC1.C(OCC)(=O)C>[CH3:8][C:6]([C:9]1[CH:10]=[C:11]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[O:12][CH2:13][C:14]1[O:15][C:1](=[S:2])[NH:17][N:16]=1)([CH3:5])[CH3:7]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 10424537HCID 10424537, compound

Product 1

HCID 11724583HCID 11724583, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Thiophosgene (0.10 mL, 1.36 mmol) is added dropwise to a -78° C. solution of [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy-acetic acid hydrazide (0.40 g, 1.36 mmol) in tetrahydrofuran (25 mL). The reaction mixture is stirred for 30 minutes, diluted with ethyl acetate, and washed three times with water and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a pale yellow oil which is crystallized from ethyl acetate/hexane yielding 0.36 g (78%) of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxymethyl]-1,3,4-oxadiazole-2(3H)-thione, mp 195.0°-196.5° C.

Workup

  1. washwashed three times with water
  2. customDrying the organic phase
  3. customover magnesium sulfate and evaporation
  4. customgives a pale yellow oil which
  5. customis crystallized from ethyl acetate/hexane yielding 0.36 g (78%) of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxymethyl]-1,3,4-oxadiazole-2(3H)-thione, mp 195.0°-196.5° C.

Sources & evidence

ORD record
ord-e6e9eaa9b2e243b69d9146ca2a1bc0b6
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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