Sulbenox → N-[7-(Hydroxyimino)-4,5,6,7-tetrahydro-1-benzothiophen-4-yl]urea

HRID 1439757Notes

Reaction equation

HRID 1439757 reaction equation
O=[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([NH:11][C:12]([NH2:14])=[O:13])[CH2:4][CH2:3]1.Cl.[NH2:16][OH:17]>N1C=CC=CC=1>[OH:17][N:16]=[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([NH:11][C:12]([NH2:14])=[O:13])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 65473SulbenoxHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 71380893N-[7-(Hydroxyimino)-4,5,6,7-tetrahydro-1-benzothiophen-4-yl]urea

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4,5,6,7-Tetrahydro-7-oxobenzo[b]thien-4-ylurea (5 g., 0.0238 mole) and hydroxylamine hydrochloride (2 g., 0.028 mole) in dry pyridine (50 ml.) are stirred together at room temperature under nitrogen overnight. The resulting clear solution is evaporated and the residual gum triturated with water (50 ml.) and the brown solid obtained is collected, washed with water and air dried (5.15 g.). The solid is recrystallized from hot methanol to afford 2.95 g. of the title compound m.p. 232°-233° C. dec.

Workup

  1. customThe resulting clear solution is evaporated
  2. customthe residual gum triturated with water (50 ml.)
  3. customthe brown solid obtained
  4. customis collected
  5. washwashed with water and air
  6. customdried (5.15 g.)
  7. customThe solid is recrystallized from hot methanol
  8. customto afford 2.95 g

Sources & evidence

ORD record
ord-a30d2750337a4d0790943d3a4837e1c6
Source dataset
uspto-grants-1977_11
Patent number
US04060627

Reaction notes

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