Water → HCID 136054869, compound

HRID 1493006Notes

Reaction equation

HRID 1493006 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:17])=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=2)=[N:4][N:3]=1.[C:22](=[N:24]S(Cl)(=O)=O)=[O:23].O>CCOCC>[CH3:16][C:13]([C:11]1[CH:12]=[C:7]([C:5]2[S:6][C:2]([NH:1][C:22]([NH2:24])=[O:23])=[N:3][N:4]=2)[CH:8]=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[OH:17])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 135518175HCID 135518175, compound

Product 1

HCID 136054869HCID 136054869, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A suspension of 4-(5-amino-1,3,4-thiadiazol-2-yl)-2,6-bis(1,1-dimethylethyl)-phenol (1.0 g, 0.0032 mole) in ether (5 ml) is added to a 0° C. solution of N-carbonylsulfamyl chloride (0.46 g, 0.0032 mole) in ether (5 ml). The resulting mixture is stirred 15 minutes before water (10 ml) is added. The mixture is diluted with ether and washed with 2M HCl and saturated aqueous NaCl. Extract with aqueous 1M NaOH (3×). The combined aqueous layers are made acidic with aqueous 2M HCl. The resulting precipitate is filtered and washed with water to provide 0.6 g (1.2 g theor., 53%) of N-[5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2-yl]-urea after drying in vacuo at 50° C.; mp >270° C.

Workup

  1. additionis added
  2. washwashed with 2M HCl and saturated aqueous NaCl
  3. extractionExtract with aqueous 1M NaOH (3×)
  4. filtrationThe resulting precipitate is filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-1291569fc4d84099bcef3a85f2a0f4b5
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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