Hydrazine hydrate (1:1) → (2-Tritylaminothiazol-4-yl)methoxyamine

HRID 2231986Notes

Reaction equation

HRID 2231986 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([CH2:26][O:27]C2C=CC=C3C(NC(=O)C=23)=O)[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:40]N>ClCCl>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([CH2:26][O:27][NH2:40])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21285061(2-Tritylamino-4-thiazolyl)methoxyphthalimide

Product 1

HCID 21285079(2-Tritylaminothiazol-4-yl)methoxyamineYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 12.0 g of the (2-tritylaminothiazol-4-yl)methoxyphthalimide in 400 ml of dichloromethane was added 1.161 g of hydrazine hydrate with cooling, and the mixture was stirred at room temperature for 5 hours. The formed precipitates were removed by filtration, the dichloromethane layer was washed with 300 ml of 10% ammonia water three times and then with 300 ml of saturated saline twice, dried on anhydrous magnesium sulfate, and concentrated to dryness to obtain 8.74 g of (2-tritylaminothiazol-4-yl)methoxyamine.

Workup

  1. temperaturewith cooling
  2. customThe formed precipitates
  3. customwere removed by filtration
  4. washthe dichloromethane layer was washed with 300 ml of 10% ammonia water three times
  5. dry with materialwith 300 ml of saturated saline twice, dried on anhydrous magnesium sulfate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-dfe3c049f62945ffa5d0780d516ca669
Source dataset
uspto-grants-1988_11
Patent number
US04785090

Reaction notes

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